


What's Your Dream?

by Blue_Five



Series: Supernatural - The Movie [3]
Category: Supernatural
Genre: M/M, Supernatural AU: Pretty Woman
Language: English
Status: Completed
Published: 2013-08-25
Updated: 2013-10-05
Packaged: 2017-12-24 13:42:35
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 10
Words: 30,916
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/940651
Author URL: https://archiveofourown.org/users/Blue_Five/pseuds/Blue_Five
Summary: <blockquote class="userstuff">
              <p>Pretty Woman AU - Dean Winchester works the streets for a living.  Castiel Novak stops for directions.  What dreams can they possibly share?</p>
            </blockquote>





	1. Dreams Deferred

**Author's Note:**

> A re-imagining of the 1990 film with a sprinkling of SPN cast members. Since it's an AU, some details may be slightly different. I hope you enjoy!
> 
> DISCLAIMER: This is a work of fiction using characters from the Supernatural/Pretty Woman universe. I do not claim any ownership. This work is solely for entertainment purposes and is not considered film or tv canon (not by a long shot).

Castiel Novak moved through the crowd of people with his usual serious, focused expression.  He smiled thinly but politely at the people who spoke to him but he did not go out of his way to make conversation. The entire event had been put together by his lawyer, Fergus Crowley. Castiel hated the 'mixers' but recognized the necessity of them for business contacts.  Now, as he listened to a very irritated female voice on his phone, he was even more reminded why interacting with people was something he truly did not enjoy.

“Meg ... Meg, I told my assistant to make the arrangements ... did she not call you?” Castiel said, pinching the bridge of his nose.

“Of course she called me, Castiel ... I talk to her more than I do you.” The sultry voice he'd once adored sounded tired and plain now.

Castiel sighed.  “I see.”  He knew where the conversation was headed and he wasn't sure what bothered him more – the end of yet another relationship or the fact that it didn't hurt as much as he thought it should.

“I have my own life, you know, Castiel,” Meg snapped. 

“This is a very important week for me, Meg.  I – I need you here.” Castiel said, trying one last time to extend his apology.

“But you never ... and I mean _never_ ... give me any notice, Castiel!”  Meg's voice turned cold.  “You just think I'm at your beck and call.”

Castiel sighed.  “I do not think you are at my beck and call, Meg ... “

“That's the way you make me feel every time you pull this shit, Castiel.  I'm seriously considering moving out.”

“If that's what you want to do, Meg,” Castiel replied tiredly.

“Fine – when you get back to New York, we'll discuss it,” Meg said reasonably.

Castiel felt a flare of irritation.  Meg was good at back-pedaling ... she'd throw him an ultimatum and then back away before anything permanent could occur.  “Now is as good a time to _discuss_ this as any, Meg.”

There was a moment of silence on the line.  Castiel imagined she had realized that she was on the verge of ending what, for her, had been a rather advantageous relationship.  He assumed she would now begin to apologize or soften the blows she had landed.  Instead, Meg surprised him.

“Fine. Good-bye, Castiel.”

The line disconnected.  Castiel blinked and regarded his mobile as though it had personally offended him.  “Good-bye, Meg.”

He tucked his phone back into his suit and sighed.  Yet another failed effort to find someone ... anyone to share his life with.  Castiel was beginning to think that perhaps he wasn't meant to have that special person to come home to ... to share his interests and his dreams.  Castiel shook his head wearily.  Did he still _have_ dreams?

* * *

“Fergus suggested that I -- “

Castiel glanced at the young man walking beside him – a young up and coming executive in his company, no doubt.  “Crowley is just my _lawyer_. He does not make decisions for this company.”

The young man swallowed hard.  “Yes sir.”

“Now then, what did the Singer stock open at on the Nikkei?” Castiel asked.

The young man looked at him blankly.  “I don't know, Mr. Novak.”

Castiel sighed.  “You don't know?”  He glanced at his watch.  “Tokyo opened approximately 90 minutes ago.  You need to keep on top of this.”

“Yes sir.”

Castiel gave a genuine smile to the young man and was pleased to see him relax.  He remembered all too well the lessons he had learned on his own climbing upward.  “It's alright but I want this wrapped up as soon as possible – I need to be back in New York by Sunday.  I have tickets to the Met.”

With that, Castiel turned and waded back into the milling crowd of people. He found the coat room and collected his long coat.  He turned when he heard his name called.  A lovely young redhead approached him with a broad smile.  Castiel returned it.

“Anna!” Castiel had dated Anna Milton some time ago and he still remembered the relationship and Anna with great fondness.  He pressed a kiss to her cheek.

“I was so sorry to hear about Michael,” Anna offered softly.

Castiel flushed but he nodded.  “Thank you.  I heard you were now married.”

Anna smiled the bashful smile of a woman in love.  “Yes ... I couldn't wait for you, Castiel.”

Castiel chuckled.  A thought ocurred to him and he turned to Anna.  “Anna ... when we were ... dating ... did you talk to my assistant more than me?”

Anna laughed, a gentle sound that Castiel had always enjoyed.  “She was one of a my bridesmaids.”

Castiel sighed and gave Anna a sad look.  Then he shook off his melancholy and gave her another kiss on the cheek.  “Your husband is a very lucky man, Anna.  Best of luck to you both.”

* * *

Crowley smiled at the lovely young woman sitting across from him.  He wondered exactly how much complimentary conversation he was going to have to make before she would sleep with him.  Opening his mouth to comment on her eyes, Crowley felt a cold hand land on his shoulder. His wife's long manicured nails dug into the muscle.   He looked up, annoyed.

“Lilith, what --”

“He's leaving ... Castiel is leaving,” Lilith said in a voice just a shade below a panic.

Standing, Crowley excused himself and walked quickly out to the drive where he'd seen Castiel disappear.  His heart – what little of it there was – fell into his shoes when he saw Castiel standing next to his lovely new Lotus Esprit.

“Oh no ... um ... Castiel?  Uh ... what seems to be the problem?  What's wrong with the limo?” Crowley chattered nervously.

Castiel gestured vaguely toward the back of the drive.  “The limo is unavailable ... the driver cannot get it out.”

The driver smiled broadly and shrugged as if to say, _Whatcha gonna do?_

“Do you have your keys?” Castiel asked.

“Uh .. yeah, here ... wait, darling, let me see if I can work something out, Castiel ... you probably shouldn't be driving ...” Crowley said frantically.

Castiel ignored him and got into the car.  He glanced over the dash and sighed.  It would have to do. 

“Castiel, are you even _familiar_ with a stick shift?”

“Of course I am, Fergus.” Castiel replied absently.  He wasn't but he had not made his way in the world by revealing his weaknesses.

Crowley groaned.  “Oh alright ... but please, dear, be _ginger_ with it ... it's rather new ... oh please, Castiel!”

Castiel braked to a stop at the end of the drive after grinding the gears into place.  “Do not worry, Fergus ... I love this car.”

“No you don't ... Castiel you'll get lost in the dark ... Beverly Hills is _down_ the hill!” Crowley shouted as Castiel turned and drove off going the wrong way.  Crowley cast a pleading look toward the sky as if to ask _Why me?_

* * *

Reaching over tiredly, Dean Winchester shut off the ringing alarm.  He stretched and yawned before flopping back against the pillow. Another night ... another couple of hundred bucks – if he was lucky.

With another yawn, Dean rolled out of bed and walked sleepily into the bathroom.  He slept nude so he just took care of mother nature then stepped into the shower and began the nightly ritual of preparing for his evening job.  Shampoo – lather, rinse, repeat.  Shave – make absolutely sure he didn't have any stubble, smooth off the chest and trim a little down below.  Use a non-scented soap that wouldn't clash with his cologne.  Check nails – trim and clean.  Dean could have slept through the entire process, he was so used to it by now. Stepping out, he brushed his teeth and checked his hair – he kept it short cropped although he did have a regular that preferred it longer.  He had a wig for those nights.

Going back into the room, Dean slid on a pair of black boxer briefs and checked himself in the mirror.  They showed off the package nicely without being too overt.  Pulling on a pair of soft, worn jeans that hugged his ass, Dean again eyed the result.  He debated for a bit over the shirt and finally decided on a fitted green button down – it brought out the color in his hazel eyes.  Tucking it in and putting on a belt, Dean unbuttoned the shirt almost halfway down his torso.  He put the non-scented lotion on to help enhance the smooth appearance and then pulled on his work boots.  For whatever reason, the johns he attracted really liked that sexy blue-collar look.  Dean didn't care as long as they paid and he could get the job done with a minimum of fuss and muss.

After making sure he had his i.d. and key tucked in the sole of his boot, Dean went back into the bathroom and pulled a couple of items from the medicine cabinet.  Leaning in close, Dean put just a small line of light brown eyeliner on and applied the clear mascara carefully. He'd learned early that clear or not, the shit burned like a mother if he got it in his eye.  After he was satisfied with the way it made his already thick lashes stand out, he put clear lip gloss over his bottom lip and pressed his lips together.  The effect, when he held his mouth open just slightly, gave him the 'pretty boy' look that Gabe called his money-making gift.  Dean studied his face in the mirror one last time.  When he was getting ready for work, Dean never made eye contact with himself in the mirror.  It was easier not to have to justify what he was doing that way.

Tucking the lip gloss in his pocket for reapplication later, Dean grabbed his black leather jacket and headed out the door.  He was halfway down the staircase when he heard the landlord berating another tenant about paying rent.  Dean groaned. He'd forgotten it was already the end of the month.  Running back to the apartment as quietly as he could, Dean went into the bathroom and lifted the lid from the back of the toilet.  He pulled out a plastic soap case to get the money he and Gabe put aside for rent each month. His stomach flipped when all he saw was a dollar bill. 

“Fuckin' _Gabe_...” Dean growled.

Unable to go out the front door, Dean went to the window beside his bed and slipped out onto the fire escape.  He lowered the ladder and climbed down to the junk-strewn 'courtyard.  Someone had cut a neat hole in the chainlink fence that surrounded the area and Dean simply ducked through it and went in search of his roommate, Gabriel.

Walking down the crowded sidewalk, Dean ignored pretty much everyone until he passed by an alleyway.  Cops and EMTs milled around the entrance and he could see a body lying just beside a dumpster.  Dean glanced over at the detective talking to a beat cop and snuck around to get a better look.  When he saw _who_ the body was, his already twisting stomach wound even tighter.  He turned away, pale, and walked on quickly.

Dean went into the club he and Gabe frequented when they weren't working – which wasn't often.  It was a place to hang out and the proprietor, Benny, was a reasonably nice guy.  He also thought Dean was 'damn cute', which got him a free beer from time to time.  Leaning over the bar, Dean shouted to be heard over the music.

“Yo, Benny!  You seen Gabe?”

Benny looked up from washing a glass and inclined his chin toward the stairs.  “In the pool room, darlin'.”

Dean grinned his thanks.  Benny was from Louisiana and his accent was thick and soft, which Dean thought was very alluring.  He'd had a casual thought about hooking up with the bartender but he didn't want to screw up a good thing which is what they had now.  No expectations, just casual friendly acquaintances – it was easier that way.

Dean went up the stairs and was not happy to see Gabe leaning back in his chair with his eyes closed and a happy little smile on his face.  The older man sitting close with his arm around Gabriel looked up and gave Dean a sly look intended to be seductive.  It just made Dean's already churning stomach threaten to erupt.  Ignoring the man, Dean looked down at his drifting roommate.

“Is it all gone?” Dean said loudly.

Gabriel opened bleary eyes and looked at Dean.  “Dean-o!  Alastair, you remember my roommate, Dean ... that's Ruby and -- “

“I know everyone!  Is it _all gone_ , Gabe?!?” Dean asked angrily.

“Alastair sold me this great shit ... we had a party ... “ Gabriel giggled. “I got to be the hostess!”

“I can't believe you bought dope with _our_ rent ... what the hell is going on with you, Gabe!” Dean snarled, walking over and grabbing Gabriel by the arm and pulling him out of his chair.

“I needed a little pick-me-up, Dean!” Gabriel said, pulling away.

Dean let go and Gabriel struggled to keep his balance.  “Yeah?  Well we need _rent money_!”

“Easy, now, Dean ...” Alastair moved to put himself between Dean and Gabriel.  “Gabe only owes me 200 more ...”

Dean blinked and stared at Gabriel who was blushing and not meeting Dean's eyes.  “ _Another_ 200 dollars?”

Gabriel gestured broadly.  “That was from way before, Dean.”

Alastair gave Dean the look again.  He seemed to be appraising Dean's body. “That's right, Dean – 200.  But if you want to work off his debt with me ... I'm sure something can be arranged.”

Gabriel rolled his eyes.  “Sweet offer, Alastair, but not now.  Come on, Dean ... downstairs.”  Taking his roommate by the arm, Gabriel dragged Dean back down to the bar.

“What would we work out, Gabe, huh?  What?” Dean demanded. “And what the hell with the money, Gabe?  You took it while I was _sleeping_?”

“You were unavailable for consultation,” Gabe replied.

“Fine ... come on ...” Dean said heading to the door.

“Snack!” Gabriel yelled.

Dean rolled his eyes and followed Gabriel to the end of the bar where he began to load up a cocktail napkin with fruit garnishes.  Dean sat beside him glumly.

“Besides ... it's my apartment,” Gabe grumbled.

“Yeah? Well I have to live there too, Gabe!”

“Look, you came here, I gave you some money, I gave you a place to stay and some valuable vocational advice.   Alastair was on my case, I had to give him somethin' so don't irritate me, Dean.”

Benny glanced down the bar and growled.  “This ain't a buffet, Gabe.”

Gabe rolled his eyes and sat back with a napkin loaded with cherries and orange slices.

“Irritate you?” Dean said incredulously.  “I just saw ... I just saw _Adam_ being pulled out of a dumpster!”

Gabe nodded sadly.  “Yeah, I know.  He was back on meth ... Uriel was trying to clean him up for months.”

Both of them turned when a fight erupted in the back of the bar.  They turned away when it didn't immediately affect them and Dean sighed. “Don't you wanna get out of here, Gabe?”

“Get outta where?  Where the fuck you wanna go?”

Dean looked down at the bartop and shook his head.  He had no idea.


	2. Transmissions & Elevators

**Notes for the Chapter:**

> DISCLAIMER: This is a work of fiction using characters from the Supernatural/Pretty Woman universe. I do not claim any ownership. This work is solely for entertainment purposes and is not considered film or tv canon (not by a long shot).

Dean stood in front of a guy selling knock-off watches from a card table. There were half a dozen of them within any given block – all peddling crap.  Dean sighed.  He wondered if he wasn't doing the same thing.  Gabriel suddenly bristled and Dean looked up to see him walking toward a dark-haired woman leaning against a tree close to the curb.

“Yo, Rachel,” Gabriel said, none too kindly.

“Yeah?” the woman said with a bored expression on her face.

Gabriel gestured at the sidewalk.  “You see the stars, babe?”

Rachel glanced down.  “Yeah, so?”

“Well, me an' Dean-o, we work Bob Hope, we work the Ritz Brothers, we work Fred Astaire -- we work all the way down to Ella Fitzgerald.  You need to move on, babe.” Gabriel said.  His shorter stature didn't make him any less intimidating when his ire was up.

“Pardon me ... I was just takin' a rest here,” Rachel said.  She looked over at Dean.  “Besides he's new.”

“Yeah, well I'm _old_ so go rest up on Monty Hall or Esther Wilson ...”

“Williams,” Dean supplied as he moved to stand behind Gabriel, one hand on his shoulder.

“Williams – where you belong!”

Rachel snorted.  “Back off, Gabe – you're gettin' to be a real grouch.” With that, she turned on her heel and sauntered away.

Gabriel turned and looked up at Dean.  His expression was concerned.  “Am I really a grouch?”

Dean could have laughed but he held it back.  “Yeah, you are.”  When Gabe's face fell, Dean added, “Just sometimes, though.”

Gabe sighed and dug one of his ever-present lollipops out of his jeans pocket.  “It's just 'cause I've got low blood sugar.”

Dean chuckled.  A red mustang full of what looked like frat boys drove by yelling the usual insults and catcalls.  Gabriel made a rude gesture and returned the insults.

The parts of the street he and Gabe worked tended to cater more toward those interested in the male body – be it a woman looking for some company or a man who didn't really want anyone to know his predilections.  Dean dealt with more of the latter, although he had a couple of regulars of the female variety.  He sighed and straightened his jacket.

“Lookin' pretty slow tonight, Gabe.”

Gabriel nodded absently.  He pulled his sucker out of his mouth and looked at Dean.  “You know ... Alastair really digs you.  He's got a lot of connections ...”

Dean was shaking his head before Gabriel could even voice his thought completely.  “Nope.  Then he'll own us and he'll take our money. No way, Gabe.”

Gabriel nodded.  “Yeah, you're right.”  He looked at Dean.  “We say who, we say when and we say how much.”

A squeal of tires pulled Gabriel's attention back to the street.  A large smile split his face.  “Yo, yo, yo Dean-o ... catch this!”

A white car turned the corner and drove jerkily past them.  Dean winced as he heard the gears grinding.  “Yikes ... that's a Lotus Esprit, Gabe.” 

“Nope, Dean, baby – that's rent!  Go get 'em tiger, you're looking exceptionally pretty tonight!” Gabe said, pushing Dean in the direction of the car which had come to a screeching halt.  “Don't take less than a hundred.  Call me when you're through, take care o' you.”

Dean looked at the car and then looked back at Gabe.  “Yeah, alright ... take care o' you,” Dean said, bumping fists with Gabe.  It was corny, but Dean still liked the feeling that he and Gabriel watched out for each other.  Every john was a potential disaster waiting to happen – if the worst did go down, at least there would be someone to identify the body and let Sam know what had happened to his moron of a brother.

Turning, Dean pulled off his jacket and swung it over one shoulder while he walked down to the car.  He grinned when he heard Gabriel's whistles behind him.

Leaning over at the open passenger side window, Dean found himself looking a rumpled, harried-looking businessman in a very expensive suit.  The man was mumbling to himself about first gear.  Dean smiled.

“Hey sugar, you lookin' for a date?” Dean said in what Gabe called his 'sex growl'. 

The man looked over at him and Dean was pinned by what had to be the bluest eyes he'd ever seen.  “No.  I am trying to locate Beverly Hills.  Can you provide me with directions?”

Dean grinned.  “Sure thing, man ... for five bucks.”

Castiel looked at the young man leaning into the car.  He was struck by the green – or were they brown – eyes set in what Castiel had to admit was a very handsome face.  Still, his demand for payment threw Castiel off-balance.  “What?  Ridiculous.”

Dean shrugged.  “Price just went up to ten.”

Castiel's eyes narrowed.  “You cannot charge me for directions.”

“Wrong, bud.  I can do whatever I want – I ain't lost.” Dean said with a smirk.  He stood and turned his back to the car, knowing his ass was level with the window.  And Dean knew it was a fine lookin' ass in the jeans he had on.

Castiel regarded the young man's back pockets for a moment.  He debated the wisdom of what he was about to do and decided that the risk was outweighed by the return. 

“Fine. Alright ... you win, I lose.  Would you have change for a twenty?”

Dean gave his best broad smile as he got into the car with a wave towards Gabe.  “For twenty, I'll show you personal.  I'll even show you where the stars live.”  He plucked the bill from Castiel's fingers and tucked it into his pocket.

Castiel sighed.  “No thank you ... a kind gentleman digging in the trash told me the way to Sylvester Stallone's house.”

“Great,” Dean said.  He glanced behind them and motioned forward.  “Down the street, make a right.”

Castiel fought the gear shift and somehow managed to get them moving without stalling the vehicle.  Dean cleared his throat as he looked forward.

“Uh ... lights ... lights would be good here,” Dean suggested.  Castiel looked around and finally managed to find the switch. 

Dean looked around the interior of the car.  He was like a kid on Christmas morning.  “This is an _awesome_ car!”

Castiel shrugged.  “It's a little ... temperamental.”

“Yours?”

“No.”

“Stolen?”

“Not precisely.”

Dean rolled his eyes.  Making conversation with this guy was like watching paint dry.  He turned his attention back to the road and listening to the engine.  Castiel cleared his throat.

“What is your name?”

Dean put on his best flirt gaze.  “Whaddya want it to be?”

Castiel pursed his lips and gave Dean a pained look.  Dean sighed.  “Dean. My name is Dean.”  He smiled at Castiel's pleased look.  “So, what hotel you stayin' at?”

“The Regent Beverly Wilshire, Dean,” Castiel replied.

“Down the block, right at the corner.” Dean directed.  He tried not to hear the gears grinding ... again.  He ran his hand over the dash. “Man ... this baby must corner like it's on rails.”

“I don't understand that reference,” Castiel said.

“Well ... come on, man!  This is the new year model – it's got a turbocharged 5 liter V-8 from a Lexus IS F!  This puppy can go from zero to 62 in 3.4 seconds!” Dean explained enthusiastically.  He winced as Castiel shifted.

“You know about cars, Dean ... where did you learn this?” Castiel asked.

“Back home ... dad was into American heavy metal – Mustangs, Corvettes, you name it.  Bought 'em cheap and fixed 'em up – I paid attention when he'd let me.”  Dean said.  “So how is it you know so _little_ about cars?”

“My first car was a limousine.” Castiel said bluntly.

Dean's eyebrows went up.  “Oh.”

“So,” Castiel said, fighting his way to the next gear.  “Where is this heavy-metal home?”

Dean, who was sitting in the passenger seat with a pained grimace on his face, muttered, “Lawrence, Kansas – you know, man, I think you left your transmission back there!  You're not shifting right.”

“I have no idea _how_ to shift correctly,” Castiel complained.  “Dean, have you ever driven a Lotus?”

Dean looked at Castiel as though he might have grown another head.  “Uh, no.”

Castiel nodded.  “You are about to begin now.”

“You're joking.”

“No. You are on my coat and this is the only way I can get you off of it.” Castiel said drily.

Dean blinked and then laughed.  “Cute.”

When Castiel had managed to pull the car over and park, Dean eagerly switched places with him.  He settled in and adjusted the mirrors to his liking.  Dean could feel the vibration from the powerful engine. He looked over at Castiel who was slipping on his seatbelt.

“Buckle up – you're about to get the ride of your life.  I'm gonna show you what this baby can _do_! You ready?” Dean asked with a broad smile.

“I am ready.”

“Alright, here we go!” Dean said as he pulled out from the curb.  He shifted smoothly and Castiel was amazed to feel how  swiftly the car traveled.  He talked while he drove to ease some of the nervousness he was feeling.  “This has pedals like a racecar ... kinda close together.  It takes a little getting used to – usually it's easier if you have smaller feet but that doesn't really matter.  Hey, did you know your foot is a big as your arm from your elbow to your wrist?”  Dean held his arm out to Castiel who stared at it and then him in succession.  “Just a little bit of trivia.”

 _Trivia? What the hell is wrong with you, Winchester?_ Dean thought.  He was _never_ this nervous with a client. Even a nerd client like this one.

“Tell me, Dean,” Castiel began as he straightened his coat.  “What sort of money does a ... young man like yourself make?  A ballpark figure.”

“I can't take less than a hundred dollars.”

“A hundred dollars a night?” Castiel asked with a considering expression.

“An hour.”

Castiel blinked.  “An _hour?_ You make a hundred dollars an hour and your jeans are almost faded white and you wear work boots?  You must be joking.”

Dean frowned at the tone in Castiel's voice.  “I don't joke about money.”

“Neither do I, Dean.” Castiel said quietly.  “A hundred dollars an hour ... rather stiff.”

Dean reached over and slid his hand between Castiel's legs.  He grinned over at the man.  “Nah, but it's got potential.”

Castiel gave him another pained look.  Dean sighed and retracted his hand. Nothing was going to happen with this one, it looked like. 

 _Too bad,_ Dean thought.  _This one was at least good-lookin'_.

Parking the car in front of the hotel, Dean got out and stood awkwardly beside the car.  Castiel draped his coat over one arm and smiled. 

“So ... here ya go,” Dean said, pointing vaguely at the hotel.

“Yes. Thank you, Dean,” Castiel paused.  “Will you be alright?”

“Who me?  Yeah, I'll just uh ... get a cab with my twenty.” Dean replied.  “See ya.”

 _Damn. All the way back home with only a twenty to show.  Fuckin' waste of a night._   Dean thought, walking over to the bus stop.  He sat on the bench and sighed, hands tucked in his jacket pockets.

Castiel regarded Dean from a distance.  He didn't differentiate between genders when he was truly attracted to someone but this ... it was ... unsettling.  Dean's eyes were so bright and when he talked about the car, his enthusiasm had been infectious. Castiel had started wanting to actually hear more.  He certainly wasn't difficult to look at ... well-built and the faded jeans definitely did show off his backside to its best advantage.  Castiel frowned and then made a decision.  He walked over to Dean.

“No taxi?”

Dean smiled.  “Nah ... I like the bus.”

“Dean ... I was curious – did you really say a hundred dollars an hour?” Castiel asked lightly.

“Yeah, I did.”

“Well, Dean ... if you don't have any prior engagements, I would be very pleased if you would accompany me into the hotel.”

Dean's smile made Castiel's heart pound.  “You got it!”  He swung his legs off the bench and moved to walk beside Castiel with his usual strut.  “So what's your name?”

“Castiel.”

“Castiel? That's a mouthful,” Dean said.

“My father was ... religious.  I am named after the angel of Thursday.” Castiel explained.

Dean's expression was priceless.  “No kidding?  I'm actually bein' picked up by an angel?  Awesome.”  Dean bumped his shoulder against Castiel's companionably.  “This is fate, Cas ... that's what this is.”

Castiel blinked.  _Cas?_

As they approached the door, Castiel unfolded his coat and began to place it across Dean's shoulders.  Dean looked at him, confused.

“Um, what's up, Cas?”

“This establishment does not rent rooms by the hour, Dean.  Your attire ...” Castiel flushed, not wanting to be overtly insulting.

Dean nodded.  “Gotcha, Cas.  No sweat.”  He pulled his arms into the beige overcoat and happened to glance upward.  What he saw stopped him in his tracks.  “Wow."  He looked around and noticed that he was woefully and wrongly dressed for just the lobby of this hotel.  The patrons looking at him made Dean feel as though a spotlight was landing directly on him and displaying every detail in sad relief.

“Dean,” Castiel's deep voice sounded next to him.  He took Dean's elbow and began to guide him toward the elevators.  “You'll be fine, Dean. Stop fidgeting.”

Dean was busy studying the pattern on the tile floor when they paused at the main desk.  He wished Castiel would just hurry up and get them to the room.  Dean couldn't stop the blush that crept into his face but when he reached the elevators with Castiel he noticed only one other couple there.  An older couple who regarded him primly.  Dean's defenses went into overdrive.  The moment the elevator opened, he swaggered past the attendant and shouted.

“Well color me happy there's a sofa in here for two!” Dean said loudly.

Castiel looked at the couple.  He sighed apologetically.  “First time in an elevator.” He explained.

The couple nodded and Castiel entered the elevator.  The attendant, a young man, smiled to himself as Castiel looked at Dean with that pained expression Dean was beginning to hate.

“Sorry, Cas ... couldn't help it.” Dean said with a laugh.

“Try,” Castiel said.  He smiled, though, so Dean didn't feel too badly.

The elevator stopped and the attendant announced, “Penthouse.”

Dean blinked and looked at Castiel with raised eyebrows.  “The penthouse?”

Castiel watched Dean walk to the door of the suite and he sighed. 

_What have I gotten myself into?_


	3. Penthouse Strawberries

**Summary for the Chapter:**

> Thanks to my readers whoever you are ... this is just fun little effort of mine and I'm glad a few of you like it too. The scene at the end is one of my favorite silly Dean moments from the tv series.

**Notes for the Chapter:**

> DISCLAIMER: This is a work of fiction using characters from the Supernatural/Pretty Woman universe. I do not claim any ownership. This work is solely for entertainment purposes and is not considered film or tv canon (not by a long shot).

Dean watched Castiel struggle with the door keycard for a moment before taking it from him and smoothly sliding it into the reader and pulling it out.  The indicator light flashed green and Dean opened the door.  He grinned and held open the door for Castiel who walked past him shaking his head.

“I miss keys.”

Dean chuckled and closed the door.  Castiel paused at a side table in the entry way to look over his mail.  Dean wandered into the hotel room proper and looked around with wide eyes.  Castiel smiled while sorting out envelopes.

“Are you impressed, Dean?”

Dean closed his mouth which had fallen slightly open in disbelief at the size of the suite.  It was bigger than any house he'd ever lived in – and far more opulently decorated.  At Castiel's voice, he fell back into the street-wise punk persona and snorted. 

“Are you kidding me, Cas?  I come here all the time – ya know, as a matter of fact they _do_ rent this room by the hour!”  Dean joked as Castiel walked past him to a desk near the balcony. 

“Of course they do, Dean,” he said with a smile.

Dean walked out onto the balcony and let out a low whistle.  The night air was refreshing and he inhaled deeply.  “Wow ... Cas, this is an awesome view!  I bet you can see all the way to the ocean from here!” Dean remarked.  He walked back into the room.

“I will take your word for it, Dean ... I do not venture out there.”

Dean frowned.  “Why not?”

“I am afraid of heights,” Castiel said.  His eyes dared Dean to make fun.

“Dude ... you're named after an _angel_ and you're scared of heights?”  Dean shook his head with a laugh. “Why do you get the penthouse then?”

“It is the best,” Castiel said as if this were obvious.  He gave a mischievous smile.  “I've looked everywhere for a penthouse on the first floor, but I cannot find one.”

Dean rolled his eyes.  “Dude, stick with the day job.”  Taking off Castiel's coat, Dean walked around the small living area looking at all the very expensive furniture.  He guessed what Castiel would be paying for this room for the week would pay Sammy's tuition for a semester.  He sighed.  Oh well, work to be done.  “So ... Cas ... now that you have me here, what _are_ you going to do with me?”

Castiel looked up from his laptop.  “I do not know precisely, Dean.  I didn't exactly plan this.”  He sat back in his chair and watched the handsome young man sauntering through his hotel room.  Dean paused and looked over at him.  Castiel felt his heart stutter when the hazel eyes met his.  In the light of the room, Castiel could better make out Dean's features.  Lightly tanned skin ... dark blonde hair and a rather toned and muscled body shown off by his unbuttoned shirt – Castiel swallowed.

Dean smiled, knowing Castiel was checking him out.  “Do you plan everything, Cas?”

“Yes, I do, Dean,” Castiel replied.

Dean pulled a chair out and straddled it.  “Yeah, me too – you know, nah, I don't really.  I'm more of a ... fly-by-the-seat-of-my-pants kinda guy.  You know – moment to moment --”  Dean's voice faded at the blank expression on Castiel's face.  He bit his lower lip then looked at Castiel again.  “You know, you could pay me – maybe that'll break the ice?”

Castiel blinked and nodded.  “Of course, Dean, I'm sorry,” he pulled his wallet from the interior of his suit jacket.  “I assume cash is acceptable?”

Dean huffed a laugh.  “Cash works for me, dude!”

Dean perched on the edge of Castiel's desk and took the hundred from him with a shy smile that usually got him a nice tip at the end of the evening.  Castiel blushed while Dean folded the bill and pushed it into his jeans pocket.  Castiel regarded Dean for a moment, then looked pointedly at where Dean sat.  “You're on my flash drive.”

Dean's eyes glinted.  “Never been on one of those before,” he said slyly.  Leaning over, Dean lifted one hip up from the desk but he did not stand. 

Castiel's blush deepened but he chuckled.  “You are ... amusing, Dean.” Reaching under Dean's hip, he pulled out the small drive. He couldn't ignore the feeling of his knuckles brushing against Dean's buttock.  Dean winked and Castiel rolled his eyes as he leaned back.

“Ok, let's see here ... “ Dean reached into his other pocket and pulled out the tools of his trade.  He held up a fan of small plastic packages.  “You got your choice, man ... I got red, green and yellow ... looks like I'm outta purple but I got one of these --” Dean held up a round gold foil package with a flourish and a wiggle of eyebrows.  “One circle coin, the condom of champions ... _nothin'_ is gettin' through this sucker!”

Castiel regarded the condoms with a stunned expression and wondered if his face could possibly get more hot.  He cleared his throat nervously and met Dean's gaze with wide blue eyes.  “Qu – quite a buffet of safety, Dean ...”

Dean chuckled and shrugged.  “Yeah, well, I'm a safe kinda guy, Cas.” For someone who'd purchased him for an hour, Dean had never seen anyone less enthusiastic about actually sleeping with him.  “Ok? Lemme get one of these on ya and we can ---”

Dean broke off as Castiel pulled away abruptly.  “Uh ... um, _no_ , Dean.  I mean ... can – can we just talk for a while?”

 _Talk?_  Dean wondered.  _What the hell is up with this guy?_

Out loud, he said, “Uh, sure, Cas – so ... you in town for business or pleasure?”

Castiel stood and took off his coat and carefully draped it over a chair. Turning to walk into the living area he sighed.  “Business ... I think.”

Dean swung himself off the desk to follow.  “Business you think.” _God, this was going to be a hard hundred._   Castiel sat in one of the oversize chairs and Dean sat in front of him on the ottoman.  “Lemmee guess ... you're a lawyer.”

“A lawyer?” Castiel said curiously.  “Why would you think that?”

Dean grinned.  “You've got that, I dunno,” he snapped his fingers as he searched for the right descriptive words.  “That sharp, useless look about you.”

Castiel laughed and Dean found himself liking the sound.  “I wouldn't want to assume, Dean, but have you _known_ a lot of lawyers?”

“Cas baby, I've known a lotta everybody ...” Dean purred.  The doorbell to the suite rang and both men stood.  “Whoa – who the hell is that?”

Castiel was trying to ignore how close their faces were and how good Dean smelled.  He cleared his throat again and said, “I assume it's the champagne, Dean.”

“Cool ... I'll just make myself useful,” Dean turned and found himself face to face with Castiel.  He stared into the impossibly cornflower blue eyes and let his eyes travel down the sharply dressed body. “Take a load off, Cas.”

Dean walked over to the door and opened it to a bellhop holding a silver tray.  He grinned at the man and stepped aside to allow him to enter. He looked over at Castiel, missing the way the bellhop's eyes traveled over him, taking in the tight jeans and revealing shirt. 

“Where ya want it, Cas?”

Castiel gestured.  “By the bar is fine.”

Dean followed the bellhop over and moved back to allow the man to leave after he'd placed the tray on the counter.  The  bellhop stepped back and said, “It will be on your statement, Mr. Novak.”

Castiel nodded. Dean stood, his attention torn between the bellhop, who hadn't moved and the strawberries he could smell on the tray.  When he realized the man was looking at him expectantly, Dean frowned and then glared.  “What are _you_ lookin' at, man?  See somethin' you like, sport?” Dean said acerbically.

Castiel got up and walked over to the uncomfortable bellhop.  He handed him a small bill and thanked him ... the man all but ran out of the suite.

Dean winced.  “Ah damn ... tip.  Missed that one ...”

“It is of no matter, Dean.” Castiel said, moving to open the champagne.

Dean sighed.  “Hey, you mind if I kick off the boots?”

“Not at all.”

Dean sat down on the steps leading to a slightly sunken seating area and pulled off his work boots.  Since he was on his feet a lot, Dean was very conscientious about keeping his boots clean and fresh smelling. Few things were less conducive to a good lay than sweaty, smelly feet.  Dean tugged his socks off and sighed as he worked his toes through the soft carpeting.

“So Cas ... you gotta wife, girlfriend?  Boyfriend?” Dean asked over his shoulder.

“I have never been married but my ex-girlfriend, Meg, is in New York moving out of my apartment as we speak,” Cas said quietly as he poured a glass of champagne.

Dean jumped up and perched on one of the barstools.  He took the glass that was offered.  “You ever _had_ a boyfriend Cas?  Cuz ...” Dean gestured up and down his own torso.

Castiel's lips quirked.  “My sexual encounters have included men, yes, Dean.”

Dean gave a smothered laugh and reached for one of the strawberries. Castiel stopped him.  When Dean frowned, Castiel gestured to the glass.  “Drink before strawberries, Dean --- the berries bring out the flavor in the champagne.”

“Oh ... cool,” Dean proceeded to drain the glass while Castiel watched. He sighed.  Dean was anything but refined.  Still, it was enjoyable to watch the young man take a bite out of a strawberry and see the resultant expression of pleasure at the sweetness.  “Wow ... that's awesome ... “

Dean looked at Castiel expectantly.  When the man did not pour himself a drink, Dean frowned.  “Uh, Cas?  You don't drink?”

“No.”

Dean grinned.  “Look, dude, I really appreciate the whole seduction scene an' all – man, those berries are good – but here's a tip: I'm a sure thing.”

Castiel blushed but he smiled.  “Yes, Dean, I am aware.”

“Well, I'm on an hourly rate – can we get a move on?”

Castiel's eyes narrowed and Dean wondered briefly if he'd just screwed himself. Instead, Castiel regarded him closely.  “I feel that the issue of time is of primary concern for you.  I would like to deal with this right now.”

Dean grinned again – he stood, putting down the glass.  “Great – let's get started!”

Castiel crossed his arms and took a step back.  Dean suddenly saw the businessman that had been hiding behind the shy nervousness.  “How much would you require for the entire night?”

“Uh .. to stay here?” Dean asked, caught off guard.  He smirked.  “You ... yeah, you can't afford that, man.”

“Try me.”

Dean met Castiel's eyes.  If the guy wanted a straight answer, Dean was going to oblige.  “Three hundred dollars.”

Castiel nodded.  “Done – now we can relax.”

Dean blinked as Castiel took his glass.  He hadn't been expecting the deal to conclude without some sort of negotiation.  Dean's brain was still trying to process that he'd just made four hundred dollars and he was still dressed.

* * *

After another glass of champagne and a few more strawberries, Dean headed to the bathroom.  It wasn't easy since he didn't carry the purse that most female hookers did, but Dean tried to keep the necessities on hand.  Condoms, lube, lip gloss, and something he could not do without when he was working. Dean went to the bathroom and pushed the door to as he called out, “Hey, that champagne kinda went to my head.  I'll be out in a sec.”

Castiel heard Dean's voice from the direction of the bathroom but he didn't understand what he'd said so he went over and pushed the door open. “I'm sorry, Dean, what did you say?”

Dean whipped around with a broad smile, his hand clenched behind his back. “Damn it, Cas ... give me a heart attack why don'tcha?  I, uh – I'll be out in a sec.”

Castiel frowned.  He could see Dean's hand clenched around something reflected in the sink mirror.  “What do you have behind your back, Dean?”

Dean blushed.  “Nothin'.”

Castiel's expression went flat and angry.  He was angry mostly with himself. “Fine.  I do not want drugs here, Dean – that is not ... please just take your money and go.”

“Drugs? Dude, I don't do drugs ... get drunk occasionally, but --” Dean protested.

“Then what is this --” Castiel asked as he jerked Dean's arm around. 

Dean winced.  “ _Ow,_ dude!  Leggo ...”

Castiel stared down at Dean's open hand.  In it lay a small foil and plastic packet – the sort that usually held mini-toothbrushes. He plucked the packet from Dean's palm, examining it as though he'd just found a diamond.

“This is ... this is a _toothbrush_ , Dean,” Castiel said, a note of wonder in his voice.

Dean snatched it back, his blush reaching his hairline.  “Yeah, so?  I ate all them damn strawberries ... the seeds'll – my mom taught me to take care of my teeth an' gums.  Happy now?”  Dean wouldn't look up.

Castiel was caught between the urge to laugh out loud and stunned silence. He opted for a polite apology.  “I am sorry, Dean.  Please ... um, please continue.”  He gestured to the sink and Dean turned his back.

“Thanks,” he grumbled.  When Castiel did not leave immediately, Dean glanced over.  “You gonna watch, man?”

“No ... it's just ... it's just that very few people surprise me, Dean,” Castiel said softly.

Dean met his eyes at that.  “Yeah?  You're lucky – most of 'em shock the hell outta me.”  He turned back to the sink and then paused. “Dude!”

“I am leaving,” Castiel said with a faint smile.  He pulled the door shut behind him. 

Not long after, Castiel looked up at an odd sound.  He crept closer to the bathroom trying to identify it and realized it was gargling. Unable to stop himself, Castiel pushed open the door and watched with a raised eyebrow as Dean stood, head thrown back.  He held a glass with a sliver of mouthwash in it – standard hotel amenity.  Dean's eyes tracked over to Castiel and he grinned broadly while still gargling.  Castiel's laugh echoed off the bathroom tiles.


	4. Bed, Breakfast and Bubbles

**Summary for the Chapter:**

> I love you all! Thanks for reading.

**Notes for the Chapter:**

> DISCLAIMER: This is a work of fiction using characters from the Supernatural universe. I do not claim any ownership. This work is solely for entertainment purposes and is not considered film or tv canon (not by a long shot).

“Yes, that may be true, but I still need numbers on Singer Industries,” Castiel said, tilting his head as he listened to the response on his mobile headset.  “Very well ... I have them from London, but the numbers from Tokyo will be next.  I will call again when I need them. Thank you.”

Tapping his headset to end the call, Castiel pulled it from his ear and looked over at Dean's laughter.  He smiled at the young man sitting on the floor in front of the TV with the remnants of the champagne and what looked like most of the candy contents of the mini-bar. Dean's legs were stretched out in front of him and he leaned back on his arms.  He occasionally nibbled on a piece of red licorice between laughs.  Castiel looked at the screen and was surprised he actually recognized the Roadrunner cartoon.  Dean's snickers burst into full-blown laughter at the antics on the TV.  Castiel made notations to himself on the report he was reviewing – iPads and laptops were all very well but Castiel preferred to work on hard copy when he was in the final negotiation stage of any project.

Dean looked over and grinned.  “Hey, Cas, I got a little carpet picnic goin' on here ... sure you don't want a drink?”

Castiel chuckled and shook his head while writing.  “I am high on life, Dean, can't you tell?”

Dean snorted, flipped over on his stomach and went back to watching the cartoon.  “ _This_ is funny, man ...”

Castiel huffed a laugh and put his report aside.  He watched, noting Dean's completely abandoned enjoyment of the moment.  He moved to another chair where he could see Dean more easily.  Dean had pulled off his shirt and Castiel studied the lines of his body.  His neck and chest arched upward gracefully as he looked up at the TV ... his spine dipping in a long, smooth line to curve upward to his backside, so enticingly clothed by the tight jeans that hugged his strong legs and finally his bare feet, crossed at the ankle.

Dean laughed again and glanced over at Castiel.  The room was dark except for the TV and the table lamp Castiel had left on.  Dean lowered his eyes but when he looked back up, Castiel was still watching him. Dean found himself feeling almost shy, an emotion he was very unfamiliar with when it came to a client.  He set the glass aside and pushed up on all fours.  His mouth quirked as he crawled over to where Castiel sat, saying nothing and just watching.  The blue eyes were intent on Dean's every move.  As Dean's hands slid up Castiel's thighs, he felt the growing arousal and a faint smile emerged.

Reaching over, Dean muted the TV and settled himself between Castiel's legs. He undid the man's tie and pulled it off before slowly unbuttoning his dress shirt.  He pulled Castiel's hips down a bit as he unzipped his pants and worked the belt open.  Castiel mused over how incredibly attractive he found Dean.  They'd met only hours before and Castiel knew less about the man than anyone he'd ever taken to bed before.  He found himself disliking the anonymity ... his thoughts were drawn back to Dean as the man leaned into Castiel and gently stroked fingertips along Castiel's jawline.  Hazel eyes drifted over Castiel's face before meeting his gaze.

“So whaddya want, Cas?” Dean said softly.

Castiel regarded Dean's expression – intent but there was a hint of a smile teasing at the corner of his lips.  He smirked.  “What do you _do,_ Dean?” Castiel asked.

The smile emerged from one side.  “Cas, baby, I do _everything_... except I don't kiss on the mouth.”  Dean's fingers were ghosting along Castiel's throat.

“Neither do I,” Castiel agreed.  

He watched the top of Dean's head as lips, far softer than Castiel would have imagined, began kissing their way down his torso.  He intended to remain more of a detached observer, but Dean's fingers slid his boxer waistband down and released his very _involved_ erection.  A sharp inhale followed as wet heat surrounded the head and Castiel's eyes slid shut.

* * *

Standing under the strong water pressure of the shower, Castiel rinsed his hair and stood wondering about the night's events.  He replayed everything in his mind and found himself smiling about most of it. Dean was indeed talented at his chosen profession.

Getting out, Castiel dried off and pulled on one of the large robes provided for his use.  Dean, Castiel noticed, slept like he did most everything else – without reservation.  He lay on his stomach with his arms tucked beneath a pillow.  His mouth was slightly open, his breathing deep and regular.  He seemed very peaceful and the hard edges of his life did not mar the handsome face for once.  Castiel smiled and went back into the other room to work.

* * *

Early the next morning, Castiel paced the room with his headset back in place.  His lawyer, Crowley was talking about Robert Singer.  Castiel chuckled.

“Of course, Singer will fight.  This company is in his blood – I doubt he's ready to have his name removed from the stationery,” Castiel said.  He signed a check for the bellhop that had just delivered breakfast.  The young man nodded and left.  Castiel sipped at a glass of orange juice while Crowley spoke.

“Castiel, darling, I don't think it's a good idea to meet with him,” Crowley said around a mouthful of toast.  He slid his hand over his cup and waved away the maid trying to refill his coffee.  “I wouldn't do this.”

Castiel chuckled.  “Of course you wouldn't, Crowley.  Set it up for this evening anyway.”

“Castiel ... it's really not a good idea for you to meet him alone,” Crowley protested.  “He's feisty ... if you say the wrong thing we could end up in court!”

“Crowley, there will always be a possibility that things will go wrong – which is why I am so fond of this.”  Castiel paused, then with a sombre tone to his voice he said, “Oh, Crowley ... about your car ...”

Dean, who was walking out of the bedroom in one of the bathrobes stopped with a frown at Castiel's words.  On the phone, Crowley groaned.  “Oh no ... what?”

“It corners like it's on rails,” Castiel said.  Dean smiled silently ... he was really starting to like this guy.

“What? What the hell are you talking about, Castiel?  Castiel?” 

Castiel ended the call and looked down at his iPad and the WSJ morning edition.  He turned when Dean said, “Uh, hi.”

“Good morning, Dean.”

Dean looked uncomfortable.  “Hey, uh – you didn't wake me ... you're busy ... give me a sec and I'll be outta your hair.”

Castiel frowned.  “There is no hurry, Dean.  Are you hungry?  I assume ... well, you should at least sit and have something to eat.”  He gestured to the table in front of him.  “I did not know what you would like so I took the liberty of ordering everything on the menu.”

Dean gawked.  Pancakes, eggs, bacon, sausage, croissants, juice, coffee ... it was like the breakfast buffet of his dreams.  Dean looked at Castiel and saw the man seriously meant for him to eat, so he grabbed a pancake, threw two sausage links on it and rolled it up.  He walked out onto the balcony while he ate.  Castiel's voice drifted after him.

“Did you sleep well, Dean?”

Dean chuckled.  “Yeah ... way too good, man.  Forgot where I was.” Dean had awakened disoriented.  The hotel sheets here were far too clean and the mattress much too soft.  The pleasant muscle aches in his body had reminded him of the activities of the previous evening. Then he'd realized he was still in bed when he should have been long gone.

Walking back into the room, Dean rolled his eyes when Castiel teased, “Forgetting your surroundings must be an occupational hazard.”

“Yeah ... somethin' like that, Cas,” Dean lifted one hip onto the table beside Castiel's morning paper and coffee.  “Did you sleep?”

Castiel bit back annoyance.  “Um, yes ... a bit ... on the couch.  I had some more work to do last night.”

Dean frowned.  “You don't sleep, you don't do drugs, you don't drink,” Dean glanced at Castiel's plate and the scattered remains of a croissant.  “You barely eat.  What do you _do_ , Cas?  Cuz I know you're not a lawyer.”

Castiel looked up at the curious hazel eyes.  It was hard to maintain any irritation but he decided to make his point anyway.  “That is correct, Dean.  There are ... four other chairs here.”  Castiel indicated the table.

“Huh? Oh ... yeah, sorry.”

Dean slid off the table and sat down quickly, ducking his head.  Castiel inwardly cursed himself for being abrupt.  Dean, however, simply made himself another sausage and pancake roll-up and poured himself a glass of orange juice.  “So ... what do you do,  Cas?” Dean's curiosity was apparently genuine.

Castiel scrolled down on his tablet before answering.  “I buy companies.”

“What kinda companies?”

Castiel looked up.  “I purchase companies that have financial difficulties.”

Dean nodded.  He swallowed.  “If they're in trouble, you get 'em for a bargain, don't ya?”

“Yes,” Castiel said with a smile.  “The company I am purchasing this week will only cost me five billion.”

Dean choked on his sausage and had to suck down a large gulp of orange juice.  “Bil – five billion _dollars?”_

“Yes.”

Dean considered this before exhaling loudly.  “Wow ... you must be a freakin' genius!”  Dean sighed.  “I only made it through 11th grade but I got my GED last year.”

Castiel saw the pride in that statement and he smiled.  Dean was a very intriguing young man.

* * *

Dean wandered into the bathroom as Castiel was getting ready.  “So, Cas ... you don't _have_ five billion dollars, do you?”

“No,” Castiel replied, working on his tie.  “Banks and investors, mostly. It takes a great deal of ... _persuading_.”

Dean considered this.  “You don't make anything and you don't build anything?”

“No,” Castiel said, annoyed that his tie was crooked.

“So what do you do with the companies once you buy 'em?”

“I sell them,” Castiel said.  

Dean slid in front of Castiel and took the tie in his hands, he deftly straightened the knot.  “So you sell them ...”

“I don't sell the entire company – I break it up into smaller pieces. That way it is worth more than the whole.”

Dean grinned.  “So it's like choppin' a boosted car and selling off the parts?”

Castiel blinked.  Hearing his life's work broken down to such simple ... and tawdry ... terms was a bit disconcerting.  “Yes ... sort of.  But my ways are _legal_.” He looked at the tie.  “Hmm ... not bad, Dean.  Not bad at all. Where did you learn to do that?”

Dean moved around Castiel.  The sound of surprise in Castiel's voice did not escape him.  Again, the smart-ass in him came out.  “Well, you know me – kinda fucked the debate team in high school.”  Castiel gave Dean a pained look.  Dean chuckled as he came back with Castiel's suit coat.  He snorted at Castiel's expression.  “Yeah, yeah ... my kid brother _was_ on the debate team.  He's smart as a whip but he couldn't put a tie on right to save his freakin' life.  Mind if I take a swim your tub before I go, Cas?”

Castiel frowned.  He found he was not as indifferent about Dean leaving as he had hoped to be.  “No ... Dean, please go ahead.”  He turned back with a faint smile.  “Stay in the shallow end.”

Dean laughed as he closed the bathroom door.

* * *

“Yes?” Castiel tapped his headset.  

“Castiel ... I'm heading out the door, darling.  Wanted you to know Singer is set for this evening.” Crowley said.

“Good,” Castiel replied.

“He's bringing his step-daughter of all things – grooming her to take over or something,” Crowley said with a hint of distaste.  

Castiel thought for a moment.  “Oh yes ... very intense young woman name Joanna.”

Crowley sighed.  “Castiel, again ... I'm not comfortable with you going alone.”

Castiel opened his mouth to say something and was interrupted by a high-pitched voice drifting from the bathroom.

_* ... lyin' alone with my head on the phone, thinkin' of you till it hurts ...*_

Curious, Castiel walked to the bathroom.  The voice continued singing.  _* ... I'm all out of love ... I'm so lost without you ... I know you right, believing for so long ...*_

“Castiel? What is that horrid noise?” Crowley asked.  “Has a cat been run over?”

Castiel smiled, looking at the scene before him.  Dean had filled the tub with bubble bath – he leaned against one side with an iPod carefully set up out of range of the water and his headphones on. His eyes were shut as he sang – Castiel was a bit confused at the choice of songs ... Dean did not strike him as an 80s love song sort of man.  All Castiel could see of him were his knees and his head poking through the mass of bubbles.

“Housekeeping is singing, Crowley.”

“Ah ... well, I wish you would at least take a date to the meeting tonight – keep it social.” Crowley said  “I know a lot of nice girls, Castiel.”

Castiel chuckled.  “No you don't, Crowley.  Besides, I have a date.”  He moved farther into the bathroom.  “Just concentrate on finding out what Singer is up to.”  Castiel ended the call and stood looking down at Dean who had a rather odd expression on his face as sang.

_*Oooh ... what are you thinkin' of ... *_

About that time, Dean opened his eyes and saw Castiel sitting on the edge of the tub with an amused look on his face.  He jerked the headphones out of his ears and blushed.  “Damn it, Cas!  You can't just sneak up on a man when he's ...”

“Singing an 80s ballad by Air Supply?”

Dean glared.  “Yeah ... whatever ... don't you knock?”

Castiel crossed his arms.  “Dean, I have a business proposition for you.”

Dean cocked an eyebrow.  “Ok, whaddya want?”

“I will be in town until Sunday.  I would like you to spend the week with me.” Castiel watched Dean's face carefully.  He was pleased to see a shy grin appear.

“Really, Cas?”

“Yes – I would hire you as an employee,” Castiel explained.  He ran an idle finger through suds on the tub edge.  “Will you consider this, Dean?  In essence, I will be paying you to be at my beck and call.”

Dean chuckled.  “Cas, as much as I'd love to be your beck and call-boy ... you're a good-lookin' rich guy.  You could get a dozen girls – or guys – for free.”

“I would like a professional ... to avoid any romantic entanglements,” Castel said.

Dean swished his hands through the bubbles.  “If you're talkin' 24 hours a day, Cas ... it'll cost ya.”

Castiel grinned.  He knew when he'd closed a deal ... now all that remained was working out the details.  “Of course, Dean.  What would you estimate your time to be worth?  A ballpark figure, as it were.”

“Six full nights ... days too ... four-thousand,” Dean said.

Castiel frowned.  “Six nights at three hundred is eighteen hundred.”

“Said you wanted days too, Cas.”

“Two thousand.”

“For this adorableness?  Three thousand.”

“Done.”

Dean blinked and slid under the sud-filled water.  Castiel heard a muffled shout and two fists broke the surface to punch the air.  Castiel laughed again.  Dean surfaced blowing suds from his lips.

“I take it that means 'yes', Dean?” Castiel asked, amused.

“Yeth ... “ Dean wiped off more bubbles.  “Yes!”

* * *

Dean got out of the tub and pulled on the robe again.  He followed Castiel through the hotel room as the man rattled off his day.

“I'll be in various meetings throughout the day, Dean.  Here ...” Drawing out his wallet, Castiel handed Dean several hundred dollar bills. “Buy some clothes.”

Dean gaped.  “Dude, don't you believe in plastic?”

Castiel continued as if he hadn't heard Dean.  “Most probably you will accompany me out during the evening – you'll need something to wear.”

“Like ...?”

“Nothing too flashy or ... sexy.  Do you understand?” Castiel glanced up at Dean, who nodded.

“Boring.”

“Conservative. Any questions?” Castiel said as he walked to the door.

Dean smirked.  “Can I call you Cassy?”

“Not if you expect me to respond, Dean.”

Smugly, Dean leaned against the wall watching Castiel.  “I woulda stayed for two-thousand, Cas.”

Castiel paused and turned back with a smile .  “I would have paid four, Dean.”

Dean laughed.  “Cas, baby, you're never gonna want to let me go.”

Castiel regarded Dean quietly.  “Dean, it's three thousand for six days and I _will_ let you go.”  He smiled again and left, closing the door behind him.

Dean stared at the door for a moment before shrugging off the melancholy that Castiel's words left in his chest.  “Maybe, dude – but I'm here now ...”

**Notes for the Chapter:**

> My description of Dean on the floor in front of the tv was inspired by an awesome pic of Jensen reading while lying shirtless on the floor. I so hope it isn't a manip because it's just ... well it's Jensen, need I say more?


	5. Rude Rodeo

**Notes for the Chapter:**

> DISCLAIMER: This is a work of fiction using characters from the Supernatural/Pretty Woman universe. I do not claim any ownership. This work is solely for entertainment purposes and is not considered film or tv canon (not by a long shot).

Dean would never admit it to anyone but he did his own version of a happy dance after Castiel closed the door.  He fell back on the bed and whooped at the ceiling.

“ _Three thousand dollars_!!” Dean shouted. 

Rolling over, Dean reached to the floor and hunted in his jeans pocket for his mobile.  He waited impatiently while the line rang.  A sleepy voice finally answered.  Dean grinned.  Gabriel was _not_ a morning person.

“Where were you last night, dude?  I called and called!”

'Kali?!??” Gabriel yelped.

“Gotcha, shortie,” Dean laughed.  He hadn't heard Gabriel talk about his on-again, off-again girlfriend in a long time.  “It's Dean.”

“Oh what the ever-lovin' fuck, Dean-o?” Gabriel groaned.  “Is the sun up?  Yes ... why am I on the phone with you instead of sleeping?”

“Oh get over it ... guess what?” Dean said, relishing his next words. “You know the guy ... the Lotus?  I'm in his hotel room in Beverly Hills ... the Penthouse!  His bathroom is bigger than the Blue Banana!”

“Do I have to hear this?” Gabriel grumbled.

“Gabe ... he wants me to stay the whole week and you know what he's gonna give me?  Guess --- you're never gonna guess,” Dean said with glee. “Three thousand dollars!”

Dean had to hold the phone away from his ear at the long streak of cursing that erupted from his roommate.  When the rant faded, Dean spoke again. 

“Plus, Gabe, he's givin' me extra money to buy clothes.”

Gabriel groaned over the line.  “Ugh, I cannot _believe_ I gave that guy to you!  Three thousand ... really?  Is he twisted?”

Dean snorted.  “Not unless you call bein' a workaholic twisted.”

“Ugly?”

“Shit no ... he's good-lookin' ... nice bod,” Dean smiled at _that_ memory.

“Well what's wrong with him?  Wait ... did he pay you?”

“End of the week,” Dean said.

It was Gabriel's turn to snort.  “ _That's_ what's wrong with him.”

Dean winced because technically Gabe could be right.  Still, he was in no position to quibble – he had three hundred cash already plus the money Castiel handed him this morning for clothes.  “Well ... he gave me the dough for last night.  Gabe – I'm gonna leave some at the front desk, ok?  You get your ass over here and pick it up.”

“Yeah, ok.”

“Gabe, I'm serious – write it down ... I'm at the Regent Beverly Wilshire – are ya writing it down?” Dean asked.

Gabriel yawned and Dean heard him scribbling – probably on a pizza box. “Reg ... Bev ... Wil ...”

“Ok, one last question ... where do I go for the clothes?  Good stuff, on him?”

Gabriel chuckled.  “In Beverly Hills, Dean-o?  Rodeo Drive, baby.”

* * *

Dean dressed quickly, he skipped the eyeliner and lip gloss but he did leave his shirt unbuttoned.  He sauntered past a man dressed in a crisp black suit and headed for the front desk, oblivious to the looks he received. Handing an envelope to the desk clerk, Dean gave her his best broad grin.  He was rewarded with a faint blushing smile.

“I'm leaving this here for a guy named Gabriel.  He'll be by to pick it up.”

“Of course, sir.”

Dean winked and walked out the front door smiling.  He didn't hear the man in the suit ask the clerk, “Ms. Wilson, do you know who that gentleman is?”

“No sir.”

The manager of the Regent Beverly Wilshire made a mental note to look for the young man if he returned to his hotel.

* * *

Dean walked down Rodeo Drive and was hard-pressed not to have his mouth open in shock at nearly everything he saw.  Store windows filled with things that sparkled and glittered pulled his attention to them.  He didn't understand the need for most of it and the prices made his breath catch in his throat – why anyone would pay over $500 for shoes was completely beyond him. The traffic that zipped by was filled with expensive cars of all makes and models.  Dean drooled over a white Aston Martin V12 Vantage Roadster until the owner came out and regarded him like he was about to be mugged.  The little man jumped into his car and drove away with a squeal of tires.  Dean snorted and walked on.

The morning was headed into noon and Dean knew he needed to find something to wear to dinner tonight soon. He chose a small store with suits of all styles hanging in the display window.  Walking in, Dean sent a quick “How _you_ doin'?” grin to the two salesmen.  He did not see the dark look they shared between them.

Dean looked at a few of the displays and tried to picture himself in the outfits.  He winced at a plaid suit and wished Sam was with him – his little brother had a better sense of conservative fashion than Dean.  Running his hands along the shoulders of the jackets, Dean realized he had absolutely no idea what size suit he wore.  He was also flabbergasted at the different fabrics and patterns – which would be appropriate for tonight?

Dean moved over to the tie display and blinked at the rainbow of colors.  He picked up one and when he lay it back down, it slithered off the table.  Dean blushed and grabbed it quickly, trying to put it back in the neat way he'd found it. 

“Shit ...” Dean muttered after the third try.

He simply roughly folded it and walked away quickly to a wall filled with, of all things, handkerchiefs.  Again, his eyes widened at the vast array of colors and sizes ... he wondered vaguely about the difference between a handkerchief and a pocket square.  A look toward the right showed him shoes of every possible variation. Dean sighed.  He was sorely tempted to find a bus to the mall and just find a JC Penney's.  Would Castiel even notice?

Walking to the racks with the suit jackets again, Dean realized he'd picked up a shadow.  He hadn't immediately registered it, but the man had been nearby every time Dean had gone to a different area of the store.  He frowned and looked up to meet an even deeper frown.  The man was tall and had dark but graying hair carefully combed back from his forehead.  His long thin face was not made softer by the frown. Dean thought he looked like the stereotypical undertaker. He crossed his arms in front of him.

“Can I _help_ you?” the man said.  His voice held just a tinge of annoyance.

“Just lookin',” Dean replied.  “You, uh ... you got nice stuff.”

“And are you ... _lookin'_ ... for something in particular?” the man asked.

Dean did not miss the snipe at his speech.  He also noticed the other, younger, sales clerk had moved to stand just to the side of the man, flanking Dean.  Dean cleared his throat nervously.  “Look, I just wanna find somethin' ... conservative.”

The man ran his gaze from Dean's scuffed work-boots up his faded jean-clad legs to his generic leather belt and exposed torso.  Dean was wearing a leather cord with a cheap gold-tone charm on it given to him by his little brother.  That got a little snobbish quirk of the mouth. Dean swallowed.  He suddenly felt woefully under-dressed and utterly ridiculous.

“I'm sure you'll find what you're looking for _elsewhere_. I very much doubt we can be of assistance.”  Dean could not miss the insult implied in the statement.

Dean pulled himself up a little straighter, intending to stand his ground.  At the movement, the two men stiffened and actually pulled back.  “Hey, easy, I just ---”

The man fixed Dean with a steady glare.  “You, young man, have obviously wandered into the wrong place.  I would advise you to leave or I will ask my assistant to call the authorities.”

Dean felt the blush work its way up his face to his hairline and ducked his head.  “Yeah, sure ... whatever.”

Moving quickly around the men, Dean escaped to the dubious safety of the walkway.  As he moved down the sidewalk, he suddenly noticed the looks and the stares from the richly dressed individuals that flowed around him.  He did not miss the way most of them gave him a wide berth.  Dean buttoned his shirt up and jammed his hands into the pockets of his jeans.  Head down, he morosely made his way back to the hotel.

* * *

Dean did not look up as he walked back into the hotel.  He didn't think he could handle seeing any more disapproving looks.  He couldn't seem to swallow the lump in his throat and he wondered how much Castiel would hate him if he just left a note and went back to Hollywood Boulevard. Walking toward the elevators, Dean startled when a man in a black suit quickly got in front of him.

“Sir? Yes ... can I help you?” Asked a commanding voice with a British accent.

“Just goin' to my room,” Dean growled moving around the man.

“Do you have a key?”

Dean snapped his fingers.  “Damn it, I forgot that little plastic thingy.”

Dean looked at the man standing between him and the elevators.  Tall with dark blonde hair precisely combed and ice-blue eyes, the man reminded him of the two salesmen he'd had the unfortunate luck to meet this morning.

“You're a guest here?” the man asked with a quirked eyebrow.

“Uh, yeah – I'm on the top floor ... I'm, uh ... with a friend.” Dean replied cautiously.

“I see ... and who would that be?”

Dean groaned inwardly.  He'd never had to get the last name of any client – he didn't even know half of his regulars' last names.  “Uh ... Castiel ... “

Dean cast around, hoping he could pull the last name from the ether of his brain.  As he did so, the elevator dinged and the attendant stepped out.  He was a nice young guy with a cute upturned nose that Dean had noticed the night before.  Dean pointed immediately.  “He knows me!”

The man in the suit snapped his fingers and motioned for the attendant to come over.  “Dennis ... are you coming off the night shift?”

“Yes sir.”

Moving to refasten the young man's uniform collar, the suit kept Dean's eyes.  “Do you know this young man?”

Eyes sliding over to Dean, the attendant looked at his employer and said, “He's with Mr. Novak.”

Dean jumped, patting Dennis on the shoulder.  “Yep, that's it!  Castiel Novak – thanks, Dennis!”  Moving around the two men, Dean walked into the elevator.  He frowned when the suit followed him a minute later and took him by the elevator.

“What? What the hell, man?” Dean protested.  The guy's grip was stronger than it looked and Dean had to move quickly to keep up with the brisk pace.  He jerked his arm out of the man's hand and sighed heavily. “Whatever ... lead on, Jeeves.”

With an annoyed glance, the man herded Dean to his office.  Dean fell heavily into a chair across from an ornate desk.  He waited for the inevitable and the man did not disappoint.

“What is your name?”

Dean snorted.  “Whaddya want it to be?”

The man paused in watering his plants and looked over sternly.  “Do not toy with me, young man.”

Dean rolled his eyes.  “Dean.”

“Thank you.  Well, Dean, allow me to explain.  Things that go on at other hotels do not happen at the Regent Beverly Wilshire.”  The man leaned against the front of the desk.  “However, Mr. Novak is a very special customer and we like to consider our special customers as ... friends.  Now, as a customer we would expect Mr. Novak to sign in any additional guests, but as a friend we are willing to overlook it.”  He looked at Dean directly.  “Now, I assume that you're a .... relative, perhaps?”

Dean blinked and nodded.

“Excellent. That would make you his ... ?”

“Cousin?”

“Of course.  Naturally, when Mr. Novak leaves I won't see you in this hotel again.”

Dean sighed.  “No.”

“I assume you have no other ... _family_ ... here?”

Dean shook his head dismally.

“Excellent, then we understand each other.  I would encourage you to perhaps dress a little more appropriately.  That will be all.”  He gestured to the door.

Dean, however, could not stop the anger that had been building since he walked out of the suit shop.   His frustration spilled over into a rambling protest. “No, dude, that ain't all!  That's what I was tryin' to do – I have all this cash and I tried to get a damn outfit on Rodeo Drive this morning and those jerks at the store made me feel like a fuckin' parolee or somethin' and I don't figure you're gonna help but I'm just sayin' I've gotta to get a suit for dinner tonight and no one gives a shit!”

Dean knew his face had to be beet red.  He bit his lip and crossed his arms over his chest to try and still his pounding heart.  He hated losing control and he hated looking weak to _anyone_. He'd managed to feel that way once today and now he'd lost his footing again.  He cursed softly as the manager picked up a phone.

“Great ... just fuckin' great ... if that's the cops, tell 'em I said 'hi'.” Dean snapped.

The man regarded Dean calmly as he held the receiver to his ear.  “Mens clothing, please ... yes, Charlie, please ... hello, this is Balthazar over at the Regent – yes, the same, how are you?” Balthazar chuckled.  “Yes, well, thank you very much ... I need a favor.  I'll be sending someone over.  His name is Dean and he's a special guest.  He's the cousin of a very special guest.”

* * *

Castiel stared at the video presentation and listened to Crowley but his mind kept drifting.  He wondered what Dean would purchase to wear tonight. He hoped it would be appropriate.  The vague memory of Dean's soft lips working their way down his body came to mind and he had to shift uncomfortably and refocus his attention on Crowley's voice.

“This is the jewel in Singer's crown ... prime industrial property straddling the port of Long Beach and Los Angeles.  We cannot overstate the real estate possibilities – I suspect we can level most of the yard,” Crowley said with a grin.  He glanced down as his phone vibrated and he frowned darkly.  Turning off the projector, Crowley looked at the other men at the table.  “What is this?  What is this?!?  Singer is working a $700 million dollar contract to build destroyers for the Navy?  I thought there was nothing in the hopper!”

One of the men looked down at his laptop and shook his head.  “There wasn't ... I mean, we didn't _think_ there was ...”

Castiel smiled inwardly as Crowley berated his team.  He poured himself a glass of water and finally broke in.  “Gentlemen, relax ... who do we know on the appropriations committee?”

Crowley thought for a moment.  “Senator Adams.”

“Fine. Contact him and we'll go from there – I assure you, the Navy is not going to spend that amount of money on _anything_ without going to appropriations.” Castiel said calmly.  “Fergus, I assume you will worry enough for both of us on this?”

Crowley nodded irritably.  “Fine.  Oh ... Castiel ... is everything set for dinner this evening?”  He followed Castiel to the door.  “Who ... who is your date again?”

Castiel chuckled.  “No one you know.”

Crowley watched Castiel uneasily as the man headed for his office.  Castiel was never so close-mouthed about mundane matters like who was accompanying him to dinner.  It did not bode well.

* * *

Dean stood in the large menswear section of yet another store.  He kept nervously adjusting his shirt and he was about to bolt when a bubbly little redhead came over to him.  “You _have_ to be Dean,” she said. “I'm Charlie.”

“Uh, yeah, hi – Balthy said you'd be nice to me ...” Dean said with another blush.

“Balthy ... I like that.  He's a great guy.”  Charlie said with a smile. “So what are your plans for tonight, Dean?”

Dean rubbed the back of his neck.  “We're gonna be going to dinner.”

“Great ... you'll need a suit.  Come on, I have something that'll look uber-sharp on you ... it'll knock the socks off your cousin.”

 _Uber-sharp_? Dean thought as the girl led him up a flight of stairs.

“Uh, Charlie?  He isn't really my cousin,” Dean said.

Charlie grinned and then winked.  “Exactly ... you're gonna look so hot he won't know what to do with himself.”

“Oh, I can probably come up with a few things ...” Dean smirked.

“Dean, I think I'm gonna like you.”

* * *

Balthazar was explaining the architecture of the hotel to one of their Asian guests when Dean appeared in front of him, a suit bag thrown over one shoulder.  “Hey, Balthy ... I got a suit for tonight.”

“And why aren't you wearing it?” Balthazar said with a thin smile.

“Didn't wanna mess it up ... hey, Charlie was great.  I wanted to say thanks.”  Dean play-punched the man's shoulder.  “You're not half-bad for a suit, Balthy.”  Dean smiled.

Balthazar returned the smile not unkindly.  “You're welcome, Dean.”

* * *

The actual room phone was ringing when Dean got the door open.  He picked it up on the third ring.  “Yel-lo!”

“Dean, do not ever pick up the phone,” Castiel said firmly.

Dean chuckled.  “Then why are you callin' me?”

“Did you get clothes today?” Castiel asked.

“Yep ... suit and tie.” Dean said proudly.

“Good. I will meet you in the lobby at 7:45 pm sharp.”

“What, you're not gonna come to the door?  Cas, I'm hurt,” Dean teased.

Castiel snorted in spite of himself.  “Dean, this isn't a _date_ .. it's business.”

“Where we goin' anyway?” Dean asked.

“A restaurant called the _Voltaire_... very high-end.”

“Fine,” Dean sighed dramatically.  “I'll meet you in the lobby but only because you're payin' me to.”

Castiel chuckled.  “I appreciate your understanding, Dean.”  Castiel ended the call and then pressed redial.  He grinned when Dean answered the phone again.  “I told you not to pick up the phone!”

“Dude, stop _calling_ me!”

Castiel laughed out loud and ended the call.  He found himself actually looking forward to evening.

* * *

Balthazar startled when Dean appeared again in the lobby.  He sighed.  “It didn't fit?”

“Huh?” Dean asked, confused.  “Oh, uh no ... it's just ... Balthy I got a problem.”

* * *

Dean stared at the shiny array of silverware.  Balthazar walked behind him.  “One more time, Dean.”

“Uh, napkin ... put in ... no wait ... _lay_ in the lap,” Dean said. 

“Good. Elbows off the table.  Don't slouch, Dean.”

Dean groaned.  He'd grown up in motel rooms eating out of paper sacks and drinking most of his beverages through a straw or straight from the bottle.  He couldn't imagine who needed three different forks to eat. He forced himself to focus again as Balthazar reviewed the placement of the silverware and its use.

“Again,” Balthazar said pointing inward toward the plate.  “Shrimp fork, salad fork, dinner fork ...”

“I got the salad fork ... but the rest ... it's a little confusing.”

“Very well, Dean ... if you get nervous ...”

“Dude, I don't get nervous ...”

“Humor me ... _dude,”_ Balthazar said with a smile.  “Count the tines ... sometimes there are four tines – dinner fork.  Sometimes there are three tines – salad fork ... “

Dean began to wonder why everyone didn't just eat soup.


	6. Gnocchi & Grand Pianos

**Notes for the Chapter:**

> DISCLAIMER: This is a work of fiction using characters from the Supernatural/Pretty Woman universe. I do not claim any ownership. This work is solely for entertainment purposes and is not considered film or tv canon (not by a long shot).

Castiel glanced over the paperwork one last time as the limo pulled up to the hotel.  As he exited to find Dean, he sent up a silent prayer that one, the young man would be ready but also that he would be dressed appropriately.  Case in hand, Castiel walked into the lobby and scanned the people there quickly.  He frowned and pulled out his  mobile, dialing the room.  Before he could press 'send', a smooth accented voice spoke to him.

“Mr. Novak?” 

Castiel looked up distractedly. “Yes?  I'm sorry but I have a call ...”

“Yes sir ... I'm the hotel manager, Balthazar, I actually have a message for you.”

Castiel paused impatiently. “Yes?  From whom?”

“Your cousin, sir.”

Castiel tapped his headset and gave the man a confused look.  “My _cousin?_ ”

“The young man who is staying with you in your room,” Balthazar said softly.

Castiel felt a bit warm but he met the man's eyes.  “I think we both know is no relation to me.”

“Of course, Mr. Novak.”

“The reason I know this is because my brother did not have any offspring,” Castiel replied.

Balthazar blinked.  _Offspring?_ He gathered himself quickly.  “Of course, sir.”

“What is the message?”

“He is waiting for you in the lounge, Mr. Novak.  He is an intriguing young man – Dean.” 

Castiel paused.  “Intriguing ... yes ... thank you -- ?” Castiel's attention was already focused elsewhere so he only vaguely heard the man respond.

“Balthazar.  I'm the manager ---”  Balthazar dropped off as Castiel walked away from him. “Honestly.”

* * *

Castiel walked into the lounge. He did not immediately see Dean and tracked his gaze over the room again, thinking he'd simply missed him.  As he glanced over the bar, Castiel did a classic double-take.  Sitting at the bar was Dean, watching him with an amused grin.  He eased off the bar stool and did a quick heel turn that made Castiel smile.

Dean felt his heart pound in his chest when Castiel smiled at him.

 _Damn if he isn't just the best lookin' guy in the room,_ Dean thought. 

Dean had dressed exactly the way Charlie had instructed him although his head had spun somewhat when she was laying everything out for him.  His suit was a dark navy pinstripe wool two-piece with a slim jacket and tapered trousers. Charlie assured him it was appropriate for day and evening wear.  His shoes were two-tone leather brogues and felt just about as comfortable as his work boots which had surprised Dean.  His tie was a simple geometric pattern with blue and green highlights and a pocket square that emphasized more of the green just peeked over the top of his lapel pocket.  Dean strolled over to Castiel, looking every inch the sophisticated young man out for a casual dinner at a high-end restaurant.

“Dude, you're late,” Dean teased.

Castiel leaned in a bit and said in a particularly gravel-laden voice, “You are stunning, Dean.”

Dean blinked.  Castiel's voice had gone straight to the part of him that didn't need to be awake right now.  He cleared his throat and smiled.  “Guess you're forgiven, Cas.”

“Shall we go to dinner, Dean?” Castiel asked.

Dean's blush at Castiel's compliment made the light dusting of freckles on his face stand out and Castiel was sorely tempted to cancel the meeting altogether so that he could examine them more closely.  Dean was handsome and somehow completely unassuming.  It was a potent mix.  Dean gave Castiel a long look with his lovely hazel eyes and smiled. 

“Lead on, Cas.”

* * *

Dean swallowed hard as they came into the restaurant.  It was breathtaking.  The decor was full of rich, warm colors and the architecture was 1920's art deco – Castiel pointed out different art pieces in the lobby that had been there since the building was completed.  Dean's eyes widened as he took in the gorgeous artwork.  When they entered the restaurant proper, the maitre’d immediately came over and welcomed them.

“Mr. Novak, welcome back.  Your table is ready and your guests have arrived.”

Dean tugged anxiously at his sleeves.

“Stop fidgeting, Dean.  You look just as handsome now as you did in the hotel,” Castiel soothed. 

Dean inhaled deeply and managed to look calm when they reached the table and Castiel greeted Robert Singer and his step-daughter, Joanna.

“Mr. Singer.”

“Yes, Mr. Novak,” Singer said, standing.  He shook Castiel's hand and then gestured toward a young blonde woman sitting at the table.  “I'm Robert Singer and this spitfire is my step-daughter, Joanna Harvelle-Singer.”

The blonde rolled her eyes affectionately and Castiel leaned toward her to shake her hand. “Pleasure to finally meet you, Mr. Novak.”

Castiel smiled.  “It's a pleasure to meet you both.  This is a friend of mine, Dean Winchester.  He will be joining us this evening.”

Dean shook Singer's hand firmly and did the same for Joanna.  “Nice to meet you, Ms. Harvelle-Singer.”

“Call me Jo,” she said brightly.  “The rest is just a mouthful that looks good on the stationery.”

Dean chuckled, relaxing a bit. The tension returned when, not moments after they'd settled at the table, Jo stood.  She motioned to her headset and whispered, “I have to take this ... dad, order for me?”

Dean wouldn't have moved had it not been for Castiel's gentle pressure on his elbow urging him up. They stood until Jo had walked away from the table and then sat again.  Dean frowned.  Castiel leaned toward him and murmured.

“It is considered respectful to stand when a lady arrives at or leaves a table.”

Dean nodded his understanding. Singer chuckled.  “Took me a while to get the hang of it too, kid.”

Dean smiled, relieved he hadn't committed some major faux pas.  The evening grew more interesting as dinner progressed.

* * *

Dean stared helplessly at the baked cheese pastry placed in front of him.  He looked at Castiel in some dismay.  Castiel smiled, guessing Dean's distress.

“The salad comes at the end of the meal, Dean.”

Dean frowned and looked back at his plate.  “But that was the fork I knew.”

Singer chuckled.  “I always wondered who needs three forks to eat a meal!”

Dean smiled at the man again.  He was beginning to like Robert Singer.  He was as impeccably dressed as Castiel but there was a hint of blue-collar hovering just below the surface.  Dean had noticed his hands earlier.  They had softened after years in a boardroom, but Robert Singer had worked hard at some point in his life – not all of the callouses were gone and there were even a few scars.  It made him feel less self-conscious about his own - working on cars for most of his life hadn't exactly given him smooth flawless gentleman's hands.  Dean was grateful it was appropriate for him to keep them in his lap.

The main course arrived and Dean watched as the waiter set a plate with what had to be the most unidentifiable food he'd ever seen.  Castiel told him during the limo ride that the restaurant was Italian.  Dean was no gourmet but the white somethings covered in bright green something and covered with dark brown somethings resembled no Italian food he knew.  Castiel had ordered for him – Dean wished he'd paid attention.  Castiel glanced over at Dean.  Another faint smile drifted across the man's face.

“It's homemade gnocchi with pesto sauce and shitake mushrooms ... try it, Dean.  It's a specialty of the restaurant and quite delicious.  Jo, please continue,” Castiel gestured toward Singer's step-daughter.

“Mr. Novak, if you were to get control ... and I don't think that you will ... what do you plan to do with the company?”  Jo fixed Castiel with a steady gaze.

Dean was half-listening as he carefully speared one of the small white knots.  He braced himself and ate the bite tentatively.

“I will break it up and sell off the pieces,” Castiel said quietly, taking a bite of his own food and looking over to Dean.

Castiel smiled when he saw the look of surprise that went across Dean's face as the flavors hit his tongue.  After probably a lifetime of fast-food, Dean's tastebuds were probably in overload.  His smile widened when Dean proceeded to attack the dish with enthusiasm.

Singer frowned.  “I'm sure you understand that I'm less than thrilled at you turning 40 years of work into a garage sale, Novak.”

Castiel shrugged.  “At the price I will pay for your stock, Mr. Singer, you will be a very rich man.”

“I'm damn well rich enough, son,” Singer said gruffly.  “I just want to run the shipyard.”

Dean was sure his eyes couldn't get any wider when the dessert was placed in front of him.  It was a fresh fruit tart with vanilla mascarpone and he thought it was the most beautiful food he'd ever seen.  Bright red strawberries circled the outer edge of the crust, followed by a ring of green kiwi then pears and peaches – raspberries and blueberries dotted the top of the tart.  Dean didn't want to cut into it because it was so pretty, but his hunger won out over the aesthetics and he speared a strawberry.  Dean was savoring the sweet flavor when he registered the conversation between Robert Singer and Castiel.

“I met your brother ... oh, what was his name?”

“Michael,” Castiel replied. Dean looked over at the flat tone in his employer's voice.

“Yes,” Singer nodded. “Michael Novak.  He wasn't quite the bastard people make him out to be.”

Castiel chuckled darkly.  “No, that would be my forte.”

“Does that make him proud of his little brother?”

Dean saw Castiel's shoulders tighten.  “I seriously doubt it.  It doesn't matter regardless ... he passed away.”

Singer frowned and Jo's eyes dropped to her plate.  “I'm sorry, I hadn't heard.”

“I'm sorry too, Cas,” Dean said softly.  He had no idea what he would do if he ever lost Sam. His little brother was everything to him.

Castiel sighed and lay his dessert fork down.  “Mr. Singer, you asked for this meeting.  What can I do for you?”

“Leave my company alone, Novak.”

“I cannot do that ... I own 10 million shares,” Castiel replied quietly.

Jo spoke up.  “We'll buy the stock back ... we're getting a contract to build destroyers.”

Dean let the waiter take away his dessert nearly untouched.  He didn't like the dark cloud that had settled over Castiel.  His body language suddenly seemed so tired and sad.  Dean found himself desperately wanting to make the gloom disappear from Castiel's face anyway he could.  He didn't examine that feeling too closely.

“There will be no destroyers ... the contract is buried with the appropriations committee.  It will remain there.” Castiel replied softly. Dean didn't get the feeling Castiel was glad of that anymore.

Jo sprang to her feet a threw her napkin down.  She leaned forward even as the men stood.  She met Castiel's eyes.  “I don't know who you think you are but I'm not going to sit here and listen to any more of this.”  Jo's gaze flicked to Dean. “It was nice meeting you, Dean.  Dad, I'm going to get some air.”

With that, Jo turned and walked out of the restaurant.  Dean stood, a little stunned.  Singer watched her leave and then turned back to Castiel.

“Watch yourself, Novak.  I'm not going down without a fight,” the older man growled.

Castiel met his opponent's eyes. “I look forward to it.”

“Good luck, young man.”

Dean sat back down quietly.  He wasn't sure what bothered him most – the unhappy expression on Castiel's face or the fact that he couldn't do anything about it.

* * *

With a yawn, Dean changed out of his suit and back into his jeans and a clean t shirt.  He hung everything up neatly.  He still couldn't believe that he'd managed to pull off a fancy dinner like that – Dean had been sure he'd do something to make Castiel throw him back out on the street.  Instead, no one had batted an eye at him.  He'd fit in and managed to look presentable, if not terribly suave.  It was a pleasant surprise for Dean – he was too used to being an outsider, unnoticed and unwanted.  He went to find Castiel and found him in a chair half in and half out of the balcony.

“Hey, Cas ... thought you never came out here,” Dean teased.

“I am only partially out – consider it a compromise,” Castiel replied.  He still looked down.

“You didn't say much on the ride home, Cas – still thinkin' about dinner?” Dean turned and pulled himself up to sit on the wall edging the balcony.  “I actually did it!  And that food ... man, that go-gochi --”

“Gnocchi,” Castiel supplied with a smile.

“Yeah, that stuff ... it was great!”  Dean grinned down at Castiel.  “I kinda got the business ... he's in trouble and you want his company.  He doesn't want to let it go.”

Castiel regarded the floor. “Thank you for the highlights, Dean.”

“Trouble is ... I think you kinda like Mr. Singer, Cas,” Dean offered quietly.

Castiel looked up at Dean.  “What I would like is for you to come down.  That wall is not intended as a seating area.”

Dean chuckled.  “What this? This makes you nervous?”  Dean began to lean backwards and Castiel paled.  “C'mon, Cas – would ya grab me before I fell?”

“Dean, I'm serious ... “ Castiel said in alarm.  He abruptly turned away.  “I will not watch!”

Dean laughed and sat back up. “Alright, alright, I'm sorry, Cas.”

Castiel rolled his eyes and glared at Dean.  Then he shook his head.  “It is irrelevant how I feel about Mr. Singer.  I cannot allow myself to become emotionally involved in business.”

“Yeah, I get that,” Dean said.  “Gabe's always tellin' me not to get attached when I turn tricks.  That's why no kissing ... too personal.  It's like what you're saying ... you stay numb, you don't get involved.”  Dean looked up at the starlit sky.  “When I'm with a john, I blank out – don't even have to think, just do it.”  Castiel raised an eyebrow and Dean froze.  His freckles stood out as he blushed furiously.  “Uh ... not with _you_ , Cas.”

“Of course not, Dean,” Castiel said with a wan smile.  He looked up into the earnest hazel eyes.  “We are not such different creatures, you and I.  We both screw people for money.”

Dean dropped his eyes, his stomach knotting.  It was one thing to know what he did for a living – to hear it spoken out loud so bluntly hurt worse than he thought it could.  He cleared his throat and cast for something to say.  Dean recalled something from dinner and looked up sadly.

“I was sorry to hear about your brother, Cas.  When did he die?” Dean asked.

“Last month,” Castiel answered.  His gaze was distant.

“Do you miss him?  God, Sammy's only up the coast five hours and I miss him more than anything,” Dean said.  His throat tightened at the thought of his little brother – or not so little anymore.

“I haven't spoken to my older brother for over fourteen years.  I was not present when he died.”

Dean looked at Castiel.  He had the same sad and tired aura around him that he'd carried in the restaurant.  Dean frowned.  “Dude, do you wanna talk about this?”

“No,” Castiel said firmly.

“Cool, I don't do chick-flick moments anyway.  But I have an idea,” Dean said eagerly, jumping down from the wall.  He crouched in front of Castiel and grinned.  “Let's break out the beer and popcorn and find a movie marathon or somethin' – hey maybe Star Wars is on demand!”

“Star Wars?” Castiel asked curiously.

Dean inhaled sharply.  “Do _not_ tell me you've never seen Star Wars!”

“Dean, I run a multi-billion dollar corporation, I've hardly had time to read a _book_ much less go to a movie --- wait, is that the film with the robots?”

Dean groaned.  “Dude, you're pathetic – come on, we'll find somethin'. We can veg out in front of the tv all night.”

“Veg out?”

“Cas, Cas, Cas ... man, you gotta learn to relax.  Veg out – be still like vegetables ... lay like broccoli,” Dean said with a laugh.

Castiel sighed with a smile.  He brushed his knuckles against Dean's jawline and was inordinately pleased when Dean leaned into the touch.  Then his smile faded and he said, “I will be back later Dean ... we can do – the vegetable thing tomorrow.”

Dean's face fell in disappointment.  “Where ya goin', Cas?  I mean, we don't _have_ to do that ... if you wanna do ... you know ...”

Castiel smiled.  “I'm just going downstairs, Dean.”

Dean frowned as Castiel walked out the door, closing it gently behind him.

* * *

Dean jerked awake to the applause on an infomercial.  Frowning, he looked at the time on the tv and was surprised to see it was almost three in the morning.  Running his hand through his hair, Dean got up and headed downstairs, still in his jeans and tshirt.  Dennis, the elevator operator, grinned when the doors opened.

“Hey dude,” Dean greeted him with a broad smile.  “You seen Mr. Novak around?”

“I'll show you,” Dennis said.

Once they reached the lobby level, Dennis peered out of the elevator to make sure no one was around and then pulled Dean over to the hotel restaurant adjacent to the lounge.  As Dean entered the room he heard someone playing the piano -- the tune was soft and melancholy at first but it seemed to lift a little at the end.  Dean inclined his chin to the night crew cleaning the room before standing behind Castiel to listen to the remainder of the piece.  He smiled, watching the play of muscles in Castiel's back and shoulders as his hands danced over the keys.  The man really was great to look at – Dean found himself captivated at the intense concentration.  It was the same way Castiel tackled everything else in his life – like there wasn't anything else in the world save what his attention was focused on. Castiel ended his piece and scattered applause came from the workers in the room.

“Thank you,” Castiel said with a faint smile.  His eyes brightened as they landed on Dean who moved to lean on the piano.  “Hello, Dean.”

“Hey, Cas.  Didn't know you played,” Dean said watching Castiel's eyes – they were so damn _blue_.

Castiel shrugged.  “I normally only play for strangers.”

Dean blinked.  Did that mean Castiel didn't consider him a stranger any longer?  He pushed the thought aside and looked down, running his fingers along the edge of the keyboard.  “I was gettin' kinda lonely upstairs.”  He moved to lean back against the piano.

Castiel looked at Dean, his expression unreadable.  He looked around the room.  “Gentleman, would you mind giving us the room?”

The workers grabbed coats and caps and walked out.  Dean watched them go with faint amusement.  “People always do what you tell them to do, Cas?”

Castiel did not respond, but he closed the cover over the keys and took Dean's hips to slide him across so he stood in front of Castiel now. Holding Dean still, Castiel leaned forward to rest his head on Dean's torso.  Dean frowned but his hand automatically came up to tangle in Castiel's thick hair, gently carding his fingers through the dark locks.  He could almost feel the ache pouring off the other man and it made him sad.

Castiel looked up into Dean's hazel eyes and then his hands were working on the button of Dean's jeans.  He unzipped the pants and ran his hand up under Dean's shirt, warm fingers sliding over the muscles. He smiled when Dean inhaled sharply. 

Dean couldn't believe how incredibly sensual Castiel's hands on him felt – he dragged in a startled breath when his hand stroked down his side.  He'd gone commando in anticipation of anything Castiel would want -- at the moment he was very grateful because his erection would have pushed very painfully against his zipper otherwise.  He looked at Castiel who was regarding him curiously and Dean realized he had his answer – people did what Castiel Novak wanted them to do and he was no different.

Castiel urged Dean's shirt upward and off while pushing his jeans down.  Dean gave a startled look around the room but no one was there.  Castiel's hands were still moving and stroking over him and suddenly Dean didn't care if all of Beverly Hills came traipsing through the room – his entire focus was on Castiel.  Dean's hand drifted from Castiel's hair to his face.  Castiel turned and kissed the palm but then he pushed Dean's hands to either side.  Dean frowned and opened his mouth to ask what Castiel wanted when lips closed over his cock. Dean groaned and arched forward.  For a guy who couldn't drive a car to save his life, Dean thought Castiel was doing a pretty good job driving him completely out of his head with his tongue.  Dean fought to keep from bucking into Castiel's mouth.  His hands slid back into Castiel's hair and Dean's head dropped back.

“Cas ... Cas ... god ... Cassss ....”

Dean heard music drifting through his mind as the building pleasure left him gasping Castiel's name.  It wasn't until later that he realized it was Castiel's composition.


	7. Retail & Other Types of Therapy

**Notes for the Chapter:**

> DISCLAIMER: This is a work of fiction using characters from the Supernatural/Pretty Woman universe. I do not claim any ownership. This work is solely for entertainment purposes and is not considered film or tv canon (not by a long shot).

"Wake up, time to shop!" Castiel said cheerfully.

Dean raised his head and blinked blearily at the man as he sat on the edge of the bed and handed Dean a black credit card. Dean took it and blinked again.

"Cas, is this thing ... _metal_?" Dean asked, studying it.

Castiel smiled. "Yes ... anodized titanium. It has no limit so you should be able to purchase everything you need. I was rather surprised you only purchased one suit yesterday."

Dean lay back against the pillow. "Yeah ... that wasn't as much fun as I thought it would be."

"Oh? Why not?"

"The guys at the store ... they made me feel like crap," Dean admitted.

Castiel studied Dean's expression and wondered at the sudden surge of anger at the salesmen who had made him feel badly about himself. He made a decision.

"Get dressed, Dean," Castiel said. "I will accompany you."

"What?"

Castiel threw Dean's t shirt at him. "Get dressed, Dean."

Dean groaned but rolled out of bed and did just that.

Walking down Rodeo Drive, Dean had his hands shoved deep in his jeans pockets and was watching his feet so he wouldn't have to see the criticizing looks from the people they passed. He was dressed in his street clothes which had been laundered but he still felt out of place.

"Come on, Cas ... let's just go back. Maybe I can find somethin' online ... people are lookin' at me, man." Dean blushed and nearly ran into Castiel when the man stopped.

Castiel tipped Dean's chin up and met his hazel eyes with a warm smile. "Dean, stores recognize money, not people and everyone is looking at me – and wondering who the handsome man beside me is," Dean snorted and blushed again. Castiel continued. "I think you will enjoy shopping today a great deal more than yesterday. Take your hands out of your pockets and don't fidget."

Dean shrugged and pulled his hands out. To his shock, Castiel took one and pulled him into the store. Dean felt his blood instantly run cold as he was surrounded by suits and shirts and ties – it was yesterday's store all over again. "Cas, I don't think I can - "

A tall, lanky man walked over to them. His face was thin and his nose and ears seemed a little too large for his head, but Dean noticed that his eyes seemed kind. That was already an improvement over yesterday – he stood close to Castiel and waited for whatever was about to happen.

"Yes, sir .. my name is Garth Fitzgerald – I'm the manager. How can I help you?"

Castiel shook Garth's hand. "Garth, this is Dean – he is in need a new wardrobe and I have chosen your shop to outfit him. Can you do this?"

Garth looked Dean over shrewdly. "I think we can manage, mister -?"

"Novak. Castiel Novak. Also, allow me to expound ... we will require more people than this to assist," Castiel said quietly, leaning toward Garth. "The reason being ... we will be spending an obscene amount of money in this store today."

Garth blinked and then a wide grin spread across his face. Dean chuckled. It never failed to amaze him when Castiel went all "corporate rich-guy" on people. He exuded a control and power which Dean could imagine had terrified more than a few rival executives. It was a stark contrast to the shy, afraid-of-heights, piano-playing man Dean had been sleeping with for the past few nights. Named for an angel, Castiel was bad ass when he wanted to be.

However, Dean wondered what he was in for when a veritable herd of salesmen descended on him and he found himself staring at a catalog filled with more clothing options than he'd dreamed existed. Castiel smiled at him and tapped his ever-present headset. Crowley's voice filled his ear.

"Castiel! Where the hell are you?! Haven't you heard – Singer is going to double your offer!" the lawyer whined loudly.

Castiel laughed. "He's countering? He is definitely tougher than I suspected. He knows the Navy contracts are stalled – where do you suppose he's getting the money?"

Crowley snorted. "I've no clue – perhaps he's throwing in with the employees."

"He'll still require someone to underwrite the paper," Castiel reminded Crowley. "Find out who that is – I will be in the office in an hour."

"Very well, Castiel." Crowley said.

Castiel turned and saw Dean being shown several different colors of shirts against suits. He looked up and his hazel eyes seemed a bit dazed. Castiel chuckled and motioned him over.

"Cas, I don't know -" Dean began.

Castiel leaned in and gently kissed Dean's cheek, effectively silencing him. "Stop saying that, Dean – you can do this. I have faith – you'll do fine. Remember ... _you_ hold the credit card so _they_ will do whatever you ask."

Dean blinked and a shy but mischievous grin crept across his face, much like the one he'd displayed when Castiel had first offered him the week's employment. It made Castiel wonder how Dean had managed to never have anyone in his life want or believe in him.

"Ok Cas ... and ... thanks," Dean said, his voice small.

Castiel tilted Dean's chin up and met his eyes. "I will see you tonight, Dean. Have _fun_."

Dean nodded. He chuckled when Castiel made a point to tell Garth, "He has my card."

Garth came over with a grin. "Well, then ... let's help you use it!"

Dean had never seen so many clothes in his entire life nor had he ever tried on so many outfits. Day suits, suits for evening, classic tuxes, the array of shoes by themselves was enough to make Dean's head explode. He nearly had a heart attack when he saw the price of a simple pair of jeans.

"Dude, they're _jeans_ ... what the hell are they made of? Gold threads?" Dean protested.

Garth simply laughed and sighed indulgently. "Dean, Dean, Dean ... the way you dress and the quality of the fabrics you choose make a difference. Expense doesn't always mean pointless ... in many cases it's because of the quality of the workmanship."

Dean understood but that didn't mean he was ever going to have a chance to live like this again and when he went back to Hollywood Boulevard, he'd be buying his jeans at the thrift store again. Garth said something that caught his attention.

"Dean, I don't know you but you seem like a nice guy so let me tell you this – you came in here with a deer in headlights look – you wouldn't even look up until Mr. Novak introduced you," Garth said. "Just now when he kissed you? Your head came up and you've got confidence oozing out of every pore. When you leave? Keep _that_ attitude. Hell, we all want to live like the Novaks of the world – but if you act like you own the place, people will generally treat you like you _do."_ Garth leaned in conspiratorially. "The clothes just help you fake it with _style_."

"Dude, I don't have to hug you or anything, do I?"

Garth laughed. "Nope ... your signature on that credit card slip is going to be all the hug I will need for the day."

Dean laughed with him and they went back to choosing shoes. Looking up, he saw a tie on one of the clerks that was unusual in color and pattern – Dean loved it. "Cas would look great in that tie!"

Garth all but tore it off the young man's neck. Dean's grin got even wider when he saw the beer and pizza come in – Garth rolled his eyes but remembered the Black Card Dean had in his possession ... and had a slice himself.

* * *

When Dean left the shop, he was wearing one of the new 'casual' outfits he'd purchased. The rest would be sent over to the hotel.

Dean had chosen a dark, navy straight-legged trouser with a striped cotton shirt and a blazer. He'd even selected a pocket square to match. The leather shoes were just as comfortable as the other pair from yesterday – for someone who spent the better part of his night walking the boulevard, Dean knew and appreciated shoes that felt good. The change in the way people looked at him was astounding but Dean wasn't really paying attention, he had a goal in mind.

Walking down the sidewalk, Dean found the shop he'd entered the day before. Steeling his features, Dean strode in, ignoring the assistant salesman and walking directly to the man he'd dealt with yesterday.

"Hello," Dean said.

"Good afternoon, sir. How may I help you?" the man's face stretched into something Dean assumed was a smile.

"Do you remember me?"

The man frowned. "No sir, I'm sorry, I'm afraid I cannot recall meeting you."

Dean smirked. He pulled out his new chest pocket wallet, exposing the new watch as well. The man looked expectantly at Dean.

"I was in here yesterday ... you threatened to call the cops on me?" Dean said with a thin smile.

"Oh ... yes, I recall ..."

"You work on commission?" Dean asked.

The man cleared his throat. "Erm ... yes."

Dean held up the Black Card and watched the man's eyes widen. "Dude – biggest mistake of your _life_. Just sayin'. Gotta go – more stuff to buy!"

With that, Dean turned on his heel and left, an absurdly broad smile covering his face. He might have done a little fist pump once out of sight, but Dean would deny it to anyone who asked. He walked back to the hotel in the best mood of his life.

* * *

In the lobby, Balthazar was talking with two employees when Dean walked in followed by a bellhop with a suit bag and several bags from various stores. He watched the young man walk to the elevator and smiled – he looked confident and well-dressed. Balthazar chuckled. Mr. Novak had no idea what he'd done.

Dean tipped the bellhop and plopped down in a chair, surrounded by boxes and bags. He sighed. Castiel had been right – it was more fun this way.

* * *

Castiel sat down at the conference table with a sigh. He looked at the reports in his hand but he didn't really see the data. Crowley was chuckling merrily to himself.

"Oh, Castiel ... you were completely right. Singer has mortgaged everything he owns to secure a bank loan!" Crowley said gleefully. "And ... it's not just any bank, my friend – it's Plymouth Trust."

Castiel began taking glasses from the tray left with a carafe of water. He made a non-committal noise.

"Castiel – it goes without saying that your business is more to them than Singer's. Make the call." Crowley tapped Castiel's phone.

Castiel stacked the glasses carefully. "Fergus, do you know what I enjoyed as a child?"

"No, Castiel ... what?"

"I enjoyed blocks. Building blocks, erector sets – I enjoyed _making_ things." Castiel said softly.

Crowley stared at him. "Castiel, pardon my bluntness but what the _hell_ is wrong with you this week? Blocks? Building things? Who the fuck cares?"

"We don't _build_ anything, Fergus. We don't _make_ anything," Castiel explained distractedly.

"We make _money_ , Castiel. This deal is a year in the making – you said this is what you wanted," Crowley said. "I'm handing it to you – the old man's throat is bared. It's time for the kill – call the bank, Castiel."

Castiel sighed. For probably the first time in his business life, he did not know what to do.

* * *

Dean had "One of These Nights" playing softly in the background as he waited for Castiel to come in the door. The lights were low -- dinner and wine were waiting. Dean was wearing his fail-safe jeans and the tie he'd gotten earlier that day. The top button was undone on the jeans -- he sat with his body profile to the door. When Castiel came in, he was intent on the mail and only looked up when Dean spoke.

"Hey Cas, how was your day?"

Dean pulled the tie down and smoothed it down his muscled chest and abdomen. A faint smile played at the corner of his mouth.

Castiel looked over and his mouth went dry as he took in the sight before him. Dean looked sexier than Castiel had ever seen him ... he was hard-pressed to remain in place. Clearing his throat, Castiel commented, "I like the tie, Dean."

"Yeah? I got it for you, Cas."

Castiel decided the mail could wait.

* * *

If anyone had suggested to him that he, Dean Winchester, would be sitting in a bathtub roughly half the size of an Olympic size swimming pool with a man whose net worth was in the billions leaning against him between his legs – Dean might have either laughed at or slugged the person. Dean was positive he was going to wake up somewhere along the way and find himself back in his old apartment with Gabe snoring in the other room. Closing his eyes and opening them quickly, Dean decided that he wasn't dreaming. Castiel's head is on one shoulder and he turned to regard Dean with a raised eyebrow at Dean's small laugh.

"Nothin' Cas, just thinking."

Dean dragged in the scent of the bubble bath surrounding them. Castiel was amused by Dean's excitement over using the bubbles again – his enthusiasm for things is infectious. Castiel lifted a hand covered in suds and blew them into the air. Dean offered up another chuckle.

"Tell me you had bubble bath as a kid, Cas – I can forgive the lack of driving experience but it's like a rite of passage or something – kids and bubble baths," Dean teased, then ran his hand over Castiel's chest. He felt the smooth skin beneath his fingertips and allowed them to slide down the line between Castiel's abs. He smiled to himself when Castiel's breath hitched. Turn-about for the piano session in Dean's opinion.

"Yes, Dean ... I had bubble baths as a child. I rather liked them," Castiel admitted softly.

Dean licked the shell of one ear. "My mom always ran mine ... she used that pink bottle ... the one with the funny-lookin' whatever on the front."

Castiel couldn't stifle a laugh at that. "Mr. Bubble ... my nanny used that as well."

"Small world, Cas," Dean grinned. "Wait ... nanny? Your mom didn't do baths or something?"

"My mother died giving birth to me, Dean."

"Oh shit, Cas ... I'm sorry, I didn't -"

Castiel reached up and gently pressed his hand against Dean's cheek. "It is alright, Dean – I have long since come to terms with it. After all, I never knew her."

Dean fell silent, berating himself for ruining the moment. He went back to dragging the washcloth across Castiel's chest and pressed a gentle kiss against the stubbled cheek.

"My brother Michael, however ... he was twelve when she died and he held it against me," Castiel said softly.

"Dude, you were a _baby_." Dean protested.

Castiel shrugged. "That did not matter to Michael ... he tormented me often whenever we saw one another even though he was an adult by the time I was old enough to understand."

Dean shook his head. "Didn't your dad do anything?"

Castiel sighed. "My father was ... absent a great deal. He died when I was still young. Michael managed my trust fund and we did not speak. I was very angry with him for a very long time."

"I guess so, dude," Dean said softly.

"It took me years and several thousand dollars in therapy to say that," Castiel said.

Dean blinked. He had his own issues and he figured he might _need_ therapy but he wasn't about to shell out good cash for some idiot behind a desk to tell him that. Castiel continued.

"I think I say it rather well – 'I was very angry with my brother'."

Dean snorted and Castiel chuckled. "Hello, my name is Mr. Novak and I am very angry with my brother ..."

Dean laughed, running his hand through Castiel's hair. "I would have been angry about the thousands of dollars."

Castiel sighed and turned his head toward Dean again. "My brother was president of the third company I ever took over. I bought it and I sold it off piece by piece."

"What'd the shrink say, Cas?" Dean asked, placing another kiss against Castiel's temple.

"He said I was cured," Castiel replied.

Dean's mouth twitched. "Well, you got him back – musta made you feel good, huh?"

Castiel fell silent and took one of Dean's hands between his own. Dean could feel Castiel's body tensing and he shifted to widen his legs a bit. His other hand snaked around Castiel and took gentle hold of his growing erection. Castiel inhaled sharply and leaned back against Dean.

"You know, Cas ... sex is the one thing I'm really, really good at – well, that and cars – but I could be considered almost an expert," Dean whispered against Cas' ear as he continued to stroke him. "Expert enough to make you forget the stress of the day - " Dean twisted his hand ever-so-slightly at the top of his stroke making Castiel moan. "Expert enough to make you forget your name -" Dean sped up his hand and Castiel gripped the sides of the tub while his head fell back against Dean's shoulder. "And expert enough to make you come so hard you see stars -" Dean's hand tightened just enough to drive Castiel over the edge with a harsh, pleading growl of Dean's name. Dean's fingers lightly slid up and down Castiel's cock, pulling a few aftershocks from him until the man slumped back, panting.

Castiel turned and regarded Dean with eyes gone cobalt in arousal. "I believe I prefer your version of therapy, Dean."

"All for the bargain-basement price of just -" Dean began. Castiel joined his voice to Dean's with a chuckle. "Three _thousand_ dollars."

They both laughed and Dean found that he wanted to laugh with Castiel a lot more.

**Notes for the Chapter:**

> Just a side note on the card Dean is using -- American Express issues the Centurion card which is anodized titanium and has no limit. It's invitation only and you have to have a net worth of over $16 million and 1.5 million in annual income. It is colloquially known as the Black Card.


	8. Chukkers and Second Chances

**Notes for the Chapter:**

> DISCLAIMER: This is a work of fiction using characters from the Supernatural universe. I do not claim any ownership. This work is solely for entertainment purposes and is not considered film or tv canon (not by a long shot).

Dean gripped the handle of the limo behind his back until his knuckles whitened.  Castiel chuckled. 

“Dean, let go,” he asked.

“What if someone recognizes me, Cas?” Dean asked in a panicked whisper.  “I can’t do this, Cas.”

Castiel laughed again.  “I doubt they will, Dean … these people do not spend much time on Hollywood Boulevard.”

“Yeah, that don’t mean anything – _you_ were there,” Dean protested.  His hands were beginning to sweat.

Castiel reached around Dean’s hips and took hold of his wrists.  “I was lost, Dean.  Please let go.”

Castiel tugged again at Dean’s wrists until he finally released the handle.  Dean looked at Cas, his hazel eyes sparkling in the sunlight and filled to the brim with worry.  Castiel leaned in and pressed a kiss between Dean's eyes.  Dean blinked and looked around wildly.  “Cas … someone’ll …”

“Dean, my sexual proclivity is no one’s business but my own.  That being said, you are not the first man I’ve spent time with in public,” Castiel explained softly.

Dean looked at the blue eyes regarding him with warmth and no little amusement.  “I’m not sure whether to be relieved or insulted by that, Cas.”

“You will notice none of _them_ are here with me today, Dean,” Castiel said.

Dean sighed.  “Alright, alright.”

“Excellent,” Castiel said.  He took Dean’s hands in his own.  “You look very handsome, Dean.  You look like a young gentleman and I promise you will have a wonderful time.  You _can_ do this.”

Dean looked at Castiel uneasily but he nodded.  Castiel pressed a kiss against Dean's jaw then took his elbow and guided him away from the limo.  “Stop fidgeting, Dean … and try to smile.”

Dean slapped his go-to confident, easy-going grin on and prayed it didn’t look too fake. 

* * *

Dean walked up to the announcer’s platform with Castiel.  Castiel smiled broadly and gestured to two women – one announcing and the other standing nearby. 

“Dean, meet Bela and Ruby – two lovely ladies who are partners in one of the most successful divorce law firms in Los Angeles.  If ever I had married, they would no doubt have ensured I was properly punished at the end of the union,” Castiel teased lightly, earning him a dark look from Bela.

Dean smiled at them both.  Castiel touched Dean’s arm briefly and walked off to greet someone he knew.  When Dean looked back, Ruby was regarding him with a smirk and Bela had turned her dark gaze on him.

“So … you’re the new flavor – Cassie must be bored.  He never brings his boys out in public,” Bela said with a sneer.

Dean kept the polite smile on his face as Bela turned away from him.  Ruby chuckled and sipped her champagne.

“Oh don't pay attention to her, she's been trying to land Castiel for years – he's one of our most eligible bachelors,” Ruby said with a laugh.

Dean smiled broadly.  “That's alright – I'm not tryin' to land Castiel ... just fuckin' him.”  He walked away before he could see the expressions on their faces.

* * *

Dean spotted Castiel standing nearby watching the polo match.  Dean had no clue how it was scored but after a play, Castiel and the crowd clapped.

Castiel shouted “Well done!”

Dean echoed him.  “Well done!”

Then he let loose a piercing whistle that startled several people around him.  Castiel laughed.  Dean’s enthusiasm was beginning to win out over his nervousness and Castiel found himself stealing more and more glances in his direction. 

Dean leaned over to Castiel.  “Remind me again why we're here?”

“Business, Dean.”

Dean looked around him.  It resembled more of a fashionable one-up contest with horses and champagne but whatever.  “So what ... you just uh, mingle?”

“Exactly.”

An accented voice called out from near a garish yellow tent.  “Castiel!”

Turning, Castiel saw Crowley waving at him with a glass of champagne.  Taking Dean's arm, he guided them over to where his lawyer stood.

“Castiel, great to see you!” Crowley gushed.

“Hello, Fergus ... I'd like to introduce you to a new friend of mine, Dean Winchester,” Castiel gently guided Dean forward with a hand in the small of his back.

Dean shook hands with the short, stocky man with a receding hairline.  The smile and handshake he got were both plastic and fake.  Dean had teased Castiel the first night about being sharp and useless but Crowley -- Dean had dealt with more than one john like Crowley ... all smiles and good-natured until they had you where they wanted you – then the humiliation started.  If you were lucky, you got out of it without the accompanying pain.

“Ah, pleased to meet you, Dean – Fergus Crowley ... this is my wife, Lilith,” Crowley introduced the thin blonde beside him. 

Lilith cocked her head to one side and gave a cold smile.  “It's always nice to meet one of Castiel's boys.”

Dean froze and Crowley cleared his throat.  “Um, dear, isn't that an acquaintance of yours?” he asked, pointing vaguely to a crowd of people farther down field.

Lilith smirked and waved as she sauntered off.  Dean held back a shudder as she walked away and he felt slightly uneasy after her comment.  Castiel said he'd spent time with other men in public.  Dean was beginning to wonder just exactly where he landed on that list.

Crowley sighed.  “Well, I didn't marry her for her tact, darlings.  Castiel let me get you something to drink,” Crowley handed his champagne flute off to Dean. “Here, kid, you can start with this.” Crowley turned back.  “Oh, Castiel?  Did you notice that Senator Adams is here?”

Castiel smiled.  “Of course I did, Crowley.  I invited him.”

Crowley smiled broadly.  “You are heaven sent, my friend – Dean, this man has my utter loyalty.  Back in a flash!”

Dean put the flute on a passing waiter's tray.  “Real stand-up guy there, Cas.  Who is he?”

“Fergus is my lawyer, Dean.  He's not so bad once you get to know him,” Castiel replied.

Dean snorted.  “Yeah ... you could freeze ice on his wife's ass.”

Castiel huffed a laugh.  “We can try that later, Dean.”

Dean looked at Castiel abruptly and saw that he was teasing.  “Cas ... you're the ultimate straight man.” Dean glanced around.  “Seriously, dude – are these people your friends?”

Castiel blinked.  “I do spend time with them, Dean.  Why?”

Dean shrugged.  “Now I know why you kept me around, Cas.”

* * *

The announcer called out for the audience to help replace divots on the field.  Dean frowned.  “What are we doing, Cas?”

“I will show you, Dean,” Castiel said.  He walked out onto the field with Dean and flipped a divot over and stomped down on it to pack it back into the ground.  “As the game progresses, the horse’s hooves punch divots into the ground.  It is tradition at the half for spectators to replace them.”

Dean shrugged.  “I'm never going to understand rich people.” 

Castiel laughed and Dean began to have fun pressing the turf back into place.  He talked idly with some of the other spectators, none of whom treated him as though he didn't belong.  Dean grinned – he was beginning to blend in.  Looking over, he saw Castiel talking with Lilith.  It made him nervous for some reason.

* * *

“He's pretty, Castiel ... wherever did you find him?” Lilith's child-like voice grated on Castiel's nerves.  He had never really liked the woman, but her comment to Dean earlier had cemented that dislike firmly in his mind.  He was not inclined to be polite so he replied glibly, “1-900-STUD” and  walked away, leaving Lilith with a blank look on her face.  It mirrored the one Bela and Ruby had displayed earlier at Dean's sarcastic comment.

Walking over to Dean, Castiel slid his arm around his waist and, in what was now a familiar gesture, pressed a kiss against Dean's cheek.  No matter how forward-thinking society might have become, Dean knew Castiel was taking a chance letting others know his sexual preferences.  Still, he couldn't find it in himself to complain when Castiel looked at him with those too-blue eyes.  He grinned and nuzzled against Castiel's ear.  Neither of them noticed the dark cloud fall over Crowley's face.

* * *

Later, Dean waited for Castiel to finish chatting with business contacts.  He heard his name called and turned to see Jo Harvelle-Singer walking over to him.  She was wearing a chocolate dress with white polka-dots and Dean thought she looked awesome.

“Dean!  I didn't know you'd be here,” Jo said cheerfully.

Dean nodded toward Castiel.  “Apparently Cas is a big sponsor to this thing ... he had to come make an “appearance”.  At least that's how he explained it to me.”

“Well, I'm glad you came,” Jo's eyes twinkled as she watched Dean.  “So … how serious is it?”

Dean looked back at her with a frown.  “What?  Me an' Cas?”  Dean shook his head.  “Nah ... it's um ... it's just casual.”

Jo smirked.  “Dean ... I've been walking these circles for most of my life and no man of Castiel's power and influence is going to bring a “casual acquaintance” to a business dinner and  then out into what is quite possibly one of the major social gatherings of the season.  I think he's taken with you.”

Dean rolled his eyes.  “Whatever ... why are you here?”

Jo pointed to one of the riders who was checking over his mount’s tack.  Dean squinted.  “Well, he's cute I guess ...”

“The _horse_ , smart-ass.” Jo snapped and then covered her mouth primly.

Dean threw his head back and laughed.  Jo blushed but before long she was laughing with him.  Neither of them noticed Fergus directing Castiel's attention to the couple.  Nor did they see the dark frown that emerged on Castiel's forehead.

* * *

“Castiel ... it's possible ... corporate espionage is not uncommon,” Crowley protested.

Castiel shook his head with a faint smile.  “Dean is not a corporate spy, Fergus.”

“Really?  I wonder because you will notice that he is awfully chummy with bloody Joanna Harvelle-Singer,” Crowley growled, pointing to the laughing couple.

Castiel swallowed hard.  He did not like the sudden surge of jealousy that rose in his gut.  He _definitely_ did not like Jo's hand on Dean's arm nor the way they laughed so companionably together.  Still, he refused to make more of it than was necessary.  It had to be nothing.

“I introduced them at dinner the other night,” Castiel reasoned.

“And now they're besties?  Castiel, this guy appears out of nowhere and suddenly he's talking to the girl whose father owns the company we're trying to buy?  A bit coincidental, don't you think?”

Castiel shook his head but Crowley continued his rail.  “Castiel, you cannot simply ignore this – he could be bringing information back to Singer ... he could be --”

“Fergus,” Castiel cut his lawyer off before he could fret any longer.  “Dean is not a spy.  He is a ... he is a prostitute.”

“Oh pull the other one, Castiel ... oh wait ... you're _serious_?” Crowley couldn't help it, he burst into laughter.  Castiel frowned.  “Castiel, you devil!  You're the only millionaire I know who goes trawling for bargain basement street walker!”

Crowley's laughter followed Castiel as he walked away toward Senator Adams who was waving at him.  “I regret telling you, Fergus,” he muttered as he pushed past his lawyer.

Crowley chuckled and wiped his eyes before zeroing in on Dean's location.  He stood alone by a tree watching the players limbering up their mounts by riding them on the field.  Crowley eased in beside him.  Dean glanced over and smiled.

“Ah, Dean ... having a good time?”

“Yeah ... yeah I'm having a great time,” Dean replied with a genuine smile.

“It must be quite a change from Hollywood Boulevard,” Crowley said softly.

Dean's smile faded.  He stared at the field but no longer saw it.  “Wh-what?”

“Oh Castiel just told me how you met ... quite amusing if you ask me.  Don't worry – your secret is safe with me, Dean.”  Crowley said with a smirk.

Dean felt frozen to the spot.  He wished he could slide into the ground and disappear.  It barely registered that Crowley was gently rubbing the back of his hand up and down Dean's arm.  Dean swallowed hard and waited for the inevitable.

“You know, Dean ... you really are pretty.  I can certainly understand Castiel's interest.  I tend to prefer the ladies myself, but I do know people who would pay quite well to spend time with you ... once Castiel leaves, that is.  Would you be interested?”

Dean looked over with a sick smile.  “Sure, dude ... why not?”

“Well, then ... I'll just be in touch.  Enjoy the rest of the match, darling,” Crowley said.  He walked away and Dean stood with his stomach in knots.  He scanned the crowd and met Castiel's eyes.  Dean looked away and wondered when the hell he was ever going to learn.

* * *

Dean followed Castiel into the hotel room.  Slamming the door, he took off his suit coat and tossed it on a chair.  Castiel frowned and looked over at Dean.

“Dean, are you alright?”

“Yeah, I'm fine, Cas.”  Dean said as he stalked into the bedroom.

Castiel sighed irritably.  “Dean, that's the seventh ‘fine’ since we left the match – I know your vocabulary is more extensive than that.”

Dean paused and glared at Castiel a moment before snarling.  “’Asshole’ – there’s an _expletive_ for our vocabulary lesson today!”  He turned on his heel and went to the closet.

“I think I preferred 'fine',” Castiel muttered to himself.

Dean toed off his shoes and stood in the middle of the bedroom.  “Just tell me one thing, Cas – why'd you bother dressin' me all up?”

Castiel frowned and walked into the bedroom.  “The clothing was appropriate, Dean --”

“No,” Dean snapped.  “What I mean is ... if you were gonna tell the whole world I'm a hooker why the hell bother to clean me up?  At least in _my_ clothes, I can handle a guy like Crowley.”

Castiel sighed again.  “Dean, I am very sorry about Crowley.  He should never have said those things.” Castiel followed Dean back into the seating area.  “He is my lawyer and I've known him for a number of years ... he thought you were a corporate spy.  He is a tad paranoid.”

Dean chuckled grimly.  “Yeah?  You gonna be my pimp now, Cas?  Newsflash -- I ain't a party favor for you and your friends!”

Dean turned to walk away, but Castiel grabbed his arm.

“Dean, I am _speaking to you_ ... I do not wish to belabor the obvious, but you are, _in fact_ , a male prostitute and currently my employee!” Castiel's voice was louder than Dean had ever heard it.

Dean pulled his arm from Castiel's grip.  “That's the way you wanna play this?  Fine – you don't _own_ me, Cas – I decide who to fuck and when!”  Dean was now shouting. 

Castiel stared at the ceiling for a moment before looking back at Dean.  When he spoke, his voice was cold and hard.  “I will not be drawn into this fight any longer, Dean.  I will not spend the next three days fighting with you.  I have expressed my apology and that _is an end to it_.”

Dean blinked.  He blinked even harder because he was surprised to feel his eyes sting with what couldn't be tears.  “I wish to fuck I'd never gotten in your stupid car, Castiel Novak.”

As he walked to the bathroom, Castiel retorted, “You had another more appealing offer that night, Dean?”

“You know what, Cas?  Bite me – you – no john _ever_ made me feel so fuckin' worthless,” Dean snarled.

“I have a very hard time believing that to be true, Dean,” Castiel replied.

Dean froze.  His throat was tight and he felt like an elephant was standing on his chest.

 _Damn it, Winchester – you never fucking learn.  Of course it got fucked – what else is new – stupid moron – you really thought this guy was –_ Dean's thoughts spun in his head.  He changed briskly back into his jeans and t shirt.  When he walked out into the sitting area, Castiel looked up.

“Where are you going, Dean?” Castiel asked, his eyes narrowing.

“I'm done, Castiel – give me what you owe me.  I'm outta here.” Dean said.  His hands were jammed deep in his pockets and he refused to meet Castiel's eyes.

Castiel frowned but then decided to cut his losses.  If Dean wanted out, he could leave.  Pulling out his wallet, Castiel counted out several bills and dropped them on the bar.  He went to look out the French doors onto the balcony.

Dean regarded the money.  It was more than he could hope to make in a month – more than enough to send to Sammy and then some.  He couldn't make his hand reach out and pick it up.  Instead, Dean wiped at what definitely wasn't a tear and walked out the door, closing it softly behind him.

Castiel glanced over at the bar when he heard the door shut.  He felt an odd sense of relief when the bills remained where he'd dropped them.  He swallowed and headed to the door.

Dean stood impatiently at the elevator, begging it to arrive so he could escape. Dean had no idea why his heart hurt so badly right now – Castiel was a john.  He was a guy who’d paid Dean to spend a week with him.  Dean sighed because he knew he’d let it go farther than that and now he was paying for it. He jammed his hands back in his pockets and hunched his shoulders when he heard the room door open.  Dean stared at the elevator button to avoid meeting Castiel's gaze.

“Dean ... I am unaccustomed to – I was not prepared to answer questions about us.  What I said was cruel and stupid – I did not mean it.” Castiel said softly.  “I would like you to remain for the week, Dean.  Will you?”

Dean looked at the floor before asking hoarsely, “Why, Cas?”

Castiel cleared his throat and replied even more softly.  “You were talking to Joanna Harvelle-Singer – laughing with her.  I-- I did not like it.”

Dean snorted.  “We were just talkin', Cas.  She's funny.”

“I did not like it, Dean.” Castiel said.  He met Dean's eyes as the young man looked up.

Dean's eyes were bright with his pain.  “You cut me pretty damn deep, Cas.”

“Yes, I did.” Castiel agreed.

Dean shook his head and regarded the man.  “Don't do it again – next time I won't look back.”

Castiel nodded and he let Dean precede him into the room.  The elevator arrived a moment after they shut the door and Dennis peered out to see no one.  He shook his head and took the car back down.

* * *

Dean arched his back, trying to pull Castiel as far into him as he could.   Castiel was a fast learner and he was getting a bit too proficient in driving Dean clean out of his mind.  One hand wrapped around his own erection, Dean looked up into the dark eyes regarding him with a heat – a _want_ \-- he’d never seen before – client or otherwise.  Dean had no experience with being _wanted_ simply for himself.  He was off-balance – the exchange from earlier had betrayed Dean’s growing feelings for Castiel.  Every time he awoke next to the man, Dean found himself smiling.  Found himself believing that maybe this might be more than just business, that Castiel might actually be seeing _Dean_.  It was dangerous to think that way … this wasn’t reality – it was money.  He was bought and paid for – nothing more, nothing less.  But as his fist sped up and dragged him over the edge into bliss, Dean let himself believe … just for this once … that maybe it could be different.   Dean tried not to hear the desperate plea in his voice as he growled out Castiel’s name.  Someone was going to get hurt in this – Dean didn’t doubt that it was going to be him.

* * *

Castiel knew he was in trouble – he was enjoying being with Dean far too much to keep things casual.  He wanted the man like he’d never wanted _anyone_.  He’d loved before, surely, but he was drawn to Dean in ways he’d never experienced previously.  He wanted to know everything about him, about his past, about his dreams – he simply _wanted_. Did that qualify as love?  Was it enough to simply want a person … Castiel refused to let himself believe he _needed_ Dean but it was rapidly becoming apparent that he was falling for the young man.  Were Dean a company, Castiel would begin finding weaknesses to exploit … he would make absolutely certain that he was in _total_ control.  Dean, however, was no faceless corporation or data to be manipulated.  He was a man with a heart and emotions.  Emotions meant complications and Castiel loathed complications. No – as he came with back arched and Dean’s name escaping in a ragged cry – Castiel knew he was in deep trouble indeed.

* * *

Lying on his stomach, Dean turned his head to look at Castiel.  He smiled when he saw Castiel was doing the same. 

“Dean,” Castiel began softly.  “You know my history … how I became who I am.  I know almost nothing about _you_.  How did you come to be in Los Angeles?”

Dean closed his eyes for a moment debating with himself about what he wanted to reveal to Castiel.  He took a deep breath and looked at Castiel who was waiting silently.

“I lost my mom when I was four, Cas.  She was beautiful and strong and man I still miss her.  Sammy, my little brother, was six months old.  I think the last sober thing my dad told me was to ‘take care of Sammy’.  He started drinking and he never stopped.  We moved around a lot and then he died when I was fifteen.” Dean paused.  “I hung in with school as long as I could but I had to drop out so I could get more hours so we could eat, have a place to sleep even if it was a dump.”

“You had no family?” Castiel asked.

“Just Sammy.  By the time he hit high school it was pretty clear that I was the pretty but dumb one and he was the hunk with a brain,” Dean said with a laugh.  “Sam got a full ride to Stanford … gonna be a lawyer just like I knew he would.  I sold my car to move out here and managed to get this far.”

“You chose _this_ as a profession?”

“No one really _plans_ this, Cas,” Dean said.  “I got out here and tried to make a go of it … waited tables, worked as a valet, tried to find a garage to work at but no luck.  I couldn’t make ends meet.  That’s when I met Gabe.  He made it sound so easy … so I did it.”

 _Never mind that I took an hour long shower and cried like a girl afterward,_ Dean thought, remembering that first time.

“Dean …”

“It’s ok, Cas – I got regulars and found something I’m good at.  Pays the bills and what extra I can, I send to Sammy.”

“Does he know what you do to earn that money?”

“Nope and no one is going to make him the wiser,” Dean said warningly.  

“You could be so much _more_ , Dean,” Castiel said. 

Dean huffed a laugh.  “Pretty but dumb, remember?  I know where I rank in the world, Cas.  People like you and Sam … you have what it takes to _do_ things – make a difference.  Me?  I’m just Dean … guy with a GED and a talent for fucking.”

Castiel swallowed the lump in his throat.  “You are so much more than what you perceive, Dean.  You are selfless and genuine.  The world has not been kind to you – and you still live every moment with such abandon and hope.  When you smile or laugh, Dean – your entire being practically _glows_ with joy.  You make me see things differently … consider other viewpoints when all I’ve ever known is my own.  And no one truly ‘dumb’ could navigate the social waters I live in – yet you have succeeded with grace and aplomb.  You are an amazing man, Dean Winchester.”

Dean felt his face grow warm and was grateful for the dark to hide his blush.  “Bad stuff is easier to believe, Cas.”

Castiel reached out and pressed his palm to Dean’s face.  “Perhaps, but that does not make it true.”


	9. Steering Wheels and Shakespeare

**Notes for the Chapter:**

> DISCLAIMER: This is a work of fiction using characters from the Supernatural universe. I do not claim any ownership. This work is solely for entertainment purposes and is not considered film or tv canon (not by a long shot).

Castiel gathered up his papers and iPad. He needed to get back to the hotel in time to change for his plans tonight. As he walked out into the lobby of Crowley’s office, Crowley moved to intercept him. 

“Castiel, what are you thinking? You didn’t sign anything!” Crowley protested. “You can’t disappear now, we’re in this too deep!”

Castiel chuckled. “Relax, Fergus … Singer isn’t going anywhere so there is no need to panic. I will be back tomorrow morning.” Glancing down at his phone, Castiel was glad to see confirmation of tickets delivered to the hotel. He turned to walk out of the office, Crowley trailing behind.

“Castiel, where on earth are you going?”

“I have a date.” Castiel said, smiling. He found himself doing that a great deal more.

“With the rent-boy?” Crowley sneered.

Castiel froze and turned to face Crowley with a dark expression. “Be cautious, Fergus.”

* * *

Castiel kissed along the line of Dean's collarbone under the hot spray of the shower. He tried not to groan too loudly as Dean's soap-slick hand drifted up and down his cock. He didn't succeed. Panting against Dean's shoulder as he came, Castiel bit down and sucked a dark mark into the warm, wet skin. Dean gasped and shivered.

“Never figured you for the whole 'marking' thing, Cas,” Dean said when Castiel's breathing was a little more even.

Castiel smiled and licked over the bruise. “Neither did I, Dean.”

Castiel's hand slid down Dean's spine and over the curve of his ass. Dean chuckled. “Thought we had to hurry up and get ready, Cas?”

Castiel sucked one of Dean's nipples through his teeth and smiled at the hiss it brought out. His hand moved between them and he began a slow, finger light stroking of Dean's very prominent erection.

“We won't be considered impolite if we are a bit late,” Castiel whispered in Dean's ear. He relished the short gasps escaping Dean's lips and truly enjoyed the faint groaning cry Dean released when he came.

Afterward, Dean stepped out of the bathroom clad in only a towel. Castiel had already pulled on his boxers and he smiled as he indicated the clothes set out for Dean. Earlier in the day, Castiel had spoken with Charlie and ordered a tuxedo for Dean along with a few ... special accessories. Dean unzipped the suit bag and grinned at the tuxedo. It was when he looked at the accessories that the broad smile Castiel enjoyed so much emerged.

“Dude, are you serious?” Dean asked, looking down at the silk bow tie, silk pocket square and the Prince of Wales checked socks.

Castiel nodded with a shy smile. “I thought you might enjoy a little ... rebellion against convention while still remaining very stylish.”

Dean laughed. The 'rebellion' Castiel spoke of was the designer's penchant for putting skulls on the accessories for his line of clothing. The tiny white craniums were subtly worked into the patterns on each piece, unnoticeable from a distance. Dean chuckled and got dressed. When he emerged from the bedroom, Castiel handed him a small box.

“Cas, you don't have to keep --”

“I wanted to Dean ... it isn't much, just cufflinks,” Castiel replied.

Dean opened the box muttering, “Dude, nothing is _just_ anything with you. I – Cas, is that ... are those _steering wheels_?” Castiel nodded. Dean suddenly looked back at the box.

“Alfred Dunhill ... hey wait, I know that name --” Dean frowned and then snapped his fingers. “Yeah! They're a British company – made um, car accessories ...”

Castiel blinked and then leaned in to put a soft kiss on the end of Dean's nose. “And this is why I tell you that you are more than what you or others perceive you to be.”

Dean blushed. “Cas, it's not like I discovered how to cure cancer or somethin'. I just know most stuff dealin' with cars.”

Castiel took Dean's wrist and fastened the cufflinks. “I was rather surprised myself when Charlie gave me a brief summary of the company founder.”

“Yeah ... he made the articulating rear view mirror,” Dean said absently as he tied his shoes. Castiel paused in putting his own bowie on and glanced over at Dean. Dean looked up at the silence. “What? Don't look at me like that, Cas ... hell, you know I like car stuff.”

Castiel finished setting the bow and shook his head. “You do not give yourself enough credit, Dean. You consider yourself to be lower in intelligence than your brother ... but it is only that your interests are not the same. Your knowledge of automobiles is not inconsiderable.”

Dean didn't look up. “Yeah, well ... bein' good at cars don't mean anything. So I can fix a carburetor. Who gives a shit? Sammy's gonna really be _helping_ people, Cas. You ... you got power and influence, Cas ... people know who you are – I see the way they fall over themselves to do whatever you want, me included. Like I said, you and Sam are the kind that change the world. Me, I just change the oil and check yer tires.”

Castiel tilted Dean's head up. “I did not mean to dampen tonight's mood, Dean. You are still amazing to me, no matter what you feel about yourself. Do you still want to go?”

“Dude, I don't even know _where_ we're going,” Dean protested.

Castiel smiled. “It is a surprise, but I think you will like it.”

“Hey, I'm game if you are,” Dean said, standing and pulling Castiel close. “And ... if I forget ... I had a really great time tonight, ok?”

Castiel cocked his head sideways and regarded Dean with amusement in his bright gaze. “Thank you, Dean. I did as well.”

* * *

Dean blinked when they pulled up to the private airstrip beside a Lear jet. “C—cas?”

Castiel turned to see Dean turning very pale. “Dean, are you alright?”

“Uh ... I-- dude ... you didn't tell me we were flying ...” Dean stammered.

“We do not have to go, Dean, it is alright. I simply never thought to ask,” Castiel replied, concerned.

Dean took a deep breath. “No ... no it's ok ... uh, there gonna be any like beverage service?”

“It has a fully stocked bar, Dean. We'll have dinner during the flight if you think you can eat?” Castiel's hand rested on Dean's arm.

“I'm gonna need a drink. A strong one,” Dean said with a weak smile.

Castiel regarded the young man for a moment. “We should go back to the hotel --”

“No!” Dean said abruptly. He looked at Castiel. “You got halfway out onto the balcony ... I can handle a flight to San Francisco.”

Castiel drew his fingers down the side of Dean's neck, eliciting a shiver. “Perhaps I can help keep you distracted.”

* * *

The flight wasn't as bad as Dean expected. He barely noticed after his first glass of whiskey and the steak dinner they were served in-flight. When they reached the Davies Symphony Hall, Dean's eyes widened. Castiel smiled and led him to the box he'd reserved. Dean looked down at the gathering musicians and the choir.

“Cas, you gotta see this,” Dean said smiling down at the stage.

“I've seen it already, Dean,” Castiel said, sitting back from the railing.

Dean chuckled. “And you get seats up here why?”

“They are the best, of course,” Castiel said.

Dean sat and looked at the program. “Car -- “

“Carmina Burana, Dean. In the 1930s Carl Orff arranged 24 poems from the Carmina Burana text into a libretto ... the theme is of the changing fortunes of life – happiness into grief, joy into bitterness and back again,” Castiel explained, his voice sliding into a rich tone Dean had never heard before. He could see Castiel's passion for the topic in his face. “It is very powerful and moving.”

Dean nodded and turned as the lights dimmed. He was unprepared for the opening movement which raised goosebumps along his arms. The next hour was nothing like the boring and dry affair he'd expected. He was actually on his feet at the closing movement. Blushing, he turned and saw that he was not alone. Many others were doing the same, Castiel included. Castiel saw the high color in Dean's face and smiled knowingly.

Dean locked his mouth on Castiel the minute they were alone in the hotel. He pushed him back toward the bed and settled himself over Castiel's frame. “Cas ...” He unbuttoned Castiel's shirt. “... that was _amazing_.” He undid Castiel's belt. “It was ... I don't even have words, dude,” He tugged boxers and pants off. “I just ... god it was just ... “Dean slid off the bed and undressed quickly before rejoining Castiel. Naked, they pressed against one another, limbs locked and both of them straining to find the perfect friction. Nipping at Castiel's bottom lip, Dean whispered. “Thank you, Cas.”

“You are welcome, Dean ... very welcome,” Castiel breathed against Dean's ear.

Afterward, lying tangled around Castiel, Dean asked. “Cas ... why don't you take the day off tomorrow? Like, _not_ go to work?”

Castiel stared at the ceiling. “I suppose I do own the company ... but _me_? _Not_ work?”

Dean laughed. “I promise ... you'll enjoy it.”

* * *

Castiel did enjoy the day. He walked in the park with Dean and ate horribly unhealthy food for lunch and dinner. Dean told him about his childhood growing up in Lawrence, Kansas. Castiel listened as Dean shared story after story about his younger brother Sam.

“You truly love Sam, don't you, Dean?”

“Yeah,” Dean agreed. “He's ... he's everything I'm not, Cas. He's the best of both of our parents. Dad might not have gotten it right later but when I was little ... he was so brave and strong. Sam's like that – maybe that's why the butted heads so much when Sammy got older. They were too much like each other.”

Castiel sighed. “Dean ... someday I hope you can see yourself as your brother probably sees you. How I see you ... you are selfless to a fault and loyal ... I doubt I would have sacrificed half as much as you for my own brother. You do not consider yourself brave but yet you took on a city you hardly knew and did what you had to in order to survive. There is more to you than you dream, Dean. So much more.”

“Whatever, Cas ... you keep sayin' that, but it doesn't change anything. I'm still a hooker and you're still ... Donald Trump,” Dean said with a smile.

Castiel rolled his eyes. “I'm far better looking than he is.”

“Ain't gonna argue _that_ , Cas.” Dean said as he watched Castiel put away his papers in the briefcase he'd lugged out to the park. “What's that, Cas?” Dean pointed to a flash of red.

Castiel smiled and drew out a thin leather-bound volume. “Meg ... my now _ex_ -girlfriend ... gave this to me when we first began dating. I would read to her from it occasionally.”

Dean took the book and looked at it before scrunching his nose. “Shakespeare? Yawn.”

“You thought classical music was boring too, Dean. Or was that not you who took charge rather ... aggressively ... last night?”

Dean blushed. “Yeah, yeah ... I didn't hear any complaints. And I can't understand half of what anyone talkin' Shakespeare says anyway.”

“Then you have not had it read correctly,” Castiel assured him. He flipped through the book and chose one of the sonnets. Clearing his throat, he read.

 

_Weary with toil, I haste me to my bed,_

_The dear repose for limbs with travail tired;_

_But then begins a journey in my head_

_To work my mind, when body’s work’s expired._

_For then my thoughts, from far where I abide,_

_Intend a zealous pilgrimage to thee,_

_And keep my drooping eyelids open wide,_

_Looking on darkness which the blind do see._

_Save that my soul’s imaginary sight_

_Presents thy shadow to my sightless view,_

_Which, like a jewel hung in ghastly night,_

_Makes black night beauteous, and her old face new._

_Lo thus by day my limbs, by night my mind,_

_For thee, and for myself, no quiet find._

Dean listened but he watched Castiel's face as he read and suddenly he found himself understanding the words. And then he _understood_ the words ... and blushed fiercely. Castiel smiled, his own face warm. It was as close as he was willing to come to admitting how he felt about Dean. He met Dean's eyes and wondered if he had gone too far. Dean had ducked his head to hide the warmth creeping across his face but he looked up shyly. “I think about you all the time too, Cas.”

* * *

Later, Dean and Castiel sat at the counter in an all-night diner eating apple pie a la mode. Dean found himself unable to stop talking but Castiel didn't seem to mind. For the first time in his life, someone was _listening_ to him. Someone was asking questions or making comments without sarcasm or condescension. Dean didn't even notice when they took one another's hand across the table until he went to gesture with both. He released Castiel's hand with something akin to disbelief. Castiel saw the look and smiled before taking hold of Dean's hand again and bringing the knuckles to his lips.

"Dude ... gettin' a little chick-flick on me again," Dean said softly - but he did not release Castiel's hand.

Castiel's smile softened even farther. "We would not want that, Dean."

"Nope ... can't have that," Dean agreed.

Dean didn't protest when they walked out of the diner still holding hands. Nor did he say anything on the limo ride back to the hotel when their fingers stayed intertwined. For once, Dean Winchester didn't feel the need to say anything at all.

* * *

Later, coming out of the bathroom after brushing his teeth, Dean chuckled when he saw Castiel leaning against the headboard, eyes shut and breathing even.

"So you finally decided to try sleepin', huh, Cas?"

Dean looked at the man who was his employer, but was rapidly becoming something else. Dean didn't examine exactly _what_ that something was - he was too far into this already. Sitting down gently beside Castiel, he studied the usually stern face relaxed and easy in sleep.  The straight nose, the soft lips now open slightly, the dark hair mussed – Dean didn't stop to think about the warmth wrapping itself around his heart.  He simply leaned in and did what he said he _never_ did ... he gently kissed Castiel on the mouth.

Blue eyes opened and Dean pulled back slightly but didn't retreat.  They studied each other for a long moment before Castiel leaned forward and claimed Dean's lips in return.  The kiss was tender and chaste at first – a light brushing of lips and tongue.  Then Castiel slid his hand into Dean's hair, pulling him closer and opening his mouth to him.  Dean's faint groan was lost in the intimate tangle of the kiss as it deepened.

Falling sideways to the bed, Dean and Castiel wrapped around one another as they struggled to get closer.  Dean's hands roamed over the smooth skin of Castiel's back and he smiled as a faint moan escaped the lips he never wanted to stop kissing.  Dean had never expected the heat growing between them and he certainly never expected the tenderness he was feeling toward Castiel.  Even more amazing was that he could feel Castiel's movements against him expressing that same tenderness and passion. All beginning with a simple kiss on the mouth.

Later, Dean lay spooned against Castiel with the man's arm lying across his hip.  Dean studied the play of shadows on the far wall and wondered when the hell he'd managed to fall head over heels in love with Castiel Novak.  He couldn't escape the fact that he was happier in this instant than he'd ever been in his life – save when his little brother Sammy came home from the hospital and regarded his older brother with trusting hazel eyes that matched his own. 

Heart full, Dean drifted off with a faint whispered, “Love you, Cas.”

Castiel Novak did not sleep for a long time.

 


	10. Awesome Deals & Angels

**Summary for the Chapter:**

> Thanks to all my readers and reviewers -- all the kudos and support get me through every story I write and I love you for it. I'm sort of sad to see this one end -- I was enjoying living the high life with the boys. Ciao darlings!

**Notes for the Chapter:**

> DISCLAIMER: This is a work of fiction using characters from the Supernatural/Pretty Woman universes. I do not claim any ownership. This work is solely for entertainment purposes and is not considered film or tv canon (not by a long shot).

With a yawn, Dean walked out into the dining area.  He wore a long dark navy robe and his boxers.  Before Castiel, Dean wouldn't have thought anything about walking around in his altogether – he smiled, thinking about everything he'd learned and how he'd changed since talking his way into a silver Lotus a week ago.  The reason for the difference in him sat scrolling through the morning WSJ and nibbling on a piece of toast with honey.  Dean watched him for a moment, watching the play of muscles beneath the dress shirt and waistcoat. He remembered the feel of those muscles, warm under his hands.  Dean swallowed hard as he recalled the previous night and what he'd admitted to Castiel.  What shocked him the most was that in the light of day – he still felt the same about the man.

“Hey, Cas ... whatcha thinkin' about out here by your lonesome?” Dean asked, pushing his reverie aside.

Castiel looked up with a faint smile.  “Good morning, Dean.  Actually, I was considering the fact that it is our last night together.  You'll be rid of me finally.”

Dean grinned broadly to hide the sudden lump in his throat.  “Yeah, Cas ... you've been pretty hard to take.”

Castiel chuckled as Dean poured himself a glass of orange juice and sat down. He picked up the print copy of the paper and found a review of the symphony opening night.  Castiel studied the young man, still amazed as ever at how handsome he truly was.  The blue robe made him appear very sophisticated without detracting from his more casual nature – Dean had found a comfortable balance.  When Dean glanced up and met his eyes, Castiel blinked and held the look.  Dean's hazel gaze was more amber in the morning light.  Castiel could lose himself just watching the shifting colors of the elder Winchester's eyes. 

“Dean ... I would like to see you again,” Castiel said softly.

Dean felt his heart slam into his rib cage.  He gave Cas a blinding smile. “You would?”

Castiel nodded.  “Yes.  I've arranged for you to have an apartment, Dean. Also, a car and a very wide variety of stores guaranteed to cater to your every shopping whim.”

Dean's smile had faltered at 'apartment' and then faded completely as he heard the rest of Castiel's plan.  His heart was tugging at him again but for an entirely different reason.  This time, it was actually breaking against the realization that Castiel saw him as just another aspect of his life – a detail to be accommodated.  Dean had no doubt Castiel cared about him, but apparently not enough to allow him to share his life.  Dean pinched the bridge of his nose and sighed.

“What else, Cas?  You gonna leave the money on the dresser when you blow through town?” Dean asked, unable to keep the bitterness out of his voice.

Castiel frowned in confusion.  He'd considered his offer very carefully and had actually been quite excited to share it with Dean.  The man's reaction was far from what he'd expected.

“Dean, it would not be like that,” Cas said.

Dean looked over at Castiel.  “Really?  What would it be like, Cas?”

Castiel pursed his lips.  “For one thing, Dean, you would no longer have to work the street to survive.”

“Yeah? That's just geography, Cas.” Dean said, getting up and walking out on the balcony.

Dean's heart was back in the same vise as when he stood at the elevator following the polo match.  The self-berating thoughts were the same too.

_Never fails, Dean, my man ... never fails.  Worst. Luck. Ever._

“Dean,” Castiel said as he walked a short way out onto the balcony.  “What do you want?  What do you see between us?”

Dean leaned on the balcony rail and looked down at the busy Beverly Hills traffic.  “I don't know, Cas.”  He raised his head and gazed across the city landscape then sighed. 

“When I was little, Cas, my mom used to tell me that angels were watching over me.  I believed her.  When the fire happened, I prayed for an angel to save my mom but she died.  Dad went sideways.  He was angry a lot of the time.  I tried to be good, Cas, I really did ... I tried to take care of Sammy and do whatever Dad told me to do.  But he'd lay into me whenever I didn't do good enough – which was a lot of the time.  Pretty but dumb, remember?” Dean looked up at the clouds.  “I thought maybe ... just maybe if I was good enough, an angel would come and take me and Sam away.  I pictured this avenging angel with huge wings and glowing eyes coming to rescue us.  Dreamed about that a lot and you know what?  The angel never mentioned anything about settin' us up in a great condo."

Castiel looked sadly at Dean as the man walked up to him, hazel eyes shining with emotion.  He startled when his mobile rang and he tapped his headset to answer it. Crowley was chuckling in his ear as Castiel watched Dean cross his arms and stare at the ground.

“Castiel, you will never guess who called me?”  Crowley chattered.  “Singer! He wants to meet with you!”

“What does he want?” Castiel asked.

“He wouldn't say, but Castiel darling, I think we have him.  His nuts are on the proverbial block, Castiel – we have him!”  Crowley snapped a towel against his counter-top.  “He's about to break – I want to have him commit his stocks this afternoon.”

Castiel frowned darkly.  “No ... if he's truly caving, I don't want to wait.  Have Singer meet me downtown this morning.  Castiel ended the call.

Turning to face Dean again, Castiel pulled on his suit jacket.  He stepped in front of the elder Winchester and tipped his chin up to meet his eyes. 

“Dean ... I have to go but I want you to know this – I did hear everything you said.  My offer ... this is all I'm capable of right now.  It's ... this is a very large step for me, Dean,” Castiel said, willing Dean to understand.

Dean straightened Castiel's tie and left his hand resting against the man's chest for a moment.  “I know, Cas.  And hey, it's an awesome deal for a guy like me.”

Castiel winced at Dean's words.  “Dean ... I've never treated you like a prostitute.”

With that, Castiel walked out of the hotel room.  Dean sighed to himself. “Ya just did, Cas.”

* * *

Dean dressed in one of the casual jean outfits he'd purchased in Garth's store.  Closer to his original clothes, but somehow different.  Dean regarded himself in the mirror.  Gone was the slouching, too thin rent-boy – he had to admit he didn't fully recognize the man who looked back at him.  Hair neatly combed, button up shirt with just enough green to bring out his eyes naturally and a fade-washed black denim jacket – Dean smiled.  He looked better than he ever had working the corners.  The smile faded when he thought about the night he'd met Castiel.  Nothing was the same now and Dean knew he was never going to be able to go back to his old life. 

Dean's mobile rang and he went to answer it.  “Yeah?”

“Yo, Dean-o!  Can you come get me?  I'm in the lobby and the undertaker with the stick up his ass won't let me pass,” Gabriel complained.

“His name is Balthazar and I'll be right down,” Dean chuckled.

* * *

Dean walked with Gabriel out poolside.  “Dude, I've been calling you all week!”

“Yeah, I know ... Benny over at the Banana told me you were lookin' for me,” Gabe said with a shrug.

“Gabe! I left you that money on Tuesday,” Dean protested.

“It's been a busy week!  Besides, I was hiding out from Alastair,” Gabe explained.

“If you picked up the money, you wouldn't have to hide, dude,” Dean teased.

“Yeah, whatever,” Gabe snorted.  “Anyway I got the money now, thank you very much for savin' my ass.  Now Alastair can get off it.”  Gabe looked over at Dean and appraised him.  “You know he was talkin' about you the other night – he would pop a vein if he saw you – I nearly didn't wanna hug you – ya might wrinkle!”

“Sure, Gabe ... notice that didn't stop you,” Dean chuckled.

“You don't look like you belong on the boulevard like that ... not that you ever really did, Dean-o,” Gabe said.  “You clean up sharp, kid.”

“Thanks, Gabe.  Easy to do when you got money,” Dean murmured.

Gabe agreed.  “So when does he leave?”

“Tomorrow.”

“You get to keep the threads?”

“Yeah.”

“Cas asked me if I wanted to see him again,” Dean said.  “But ... nah, I don't think so.”

“You don't think so,” Gabe repeated.  He looked at Dean's face.  “Oh man, you're kidding.”

“What?” Dean asked with a frown.

“I know this downtrodden broken-hearted look on your face,” Gabriel said, squinting at Dean.

“Oh bite me, Gabriel.  I'm not broken-hearted.”

“You fell for him, didn't you?”

“Gabe, shut up – please,” Dean rolled his eyes.  “I did not fall for him, that's just dumb.”

“Did you kiss him?  On the mouth?” Gabe asked pointedly.

Dean blushed.  “Yeah ... it was nice.”

“What the fuck, Dean?  You fall in love and kiss him on the mouth, did I not teach you _anything_?” Gabriel said, exasperated.

“Look, I ain't stupid ... I'm _not_ in love with him.  I'm not,” Dean said firmly.

“Say it one more time, Dean-o, maybe you'll believe yourself,” Gabriel chided.  “You definitely like him.”

“Yeah ... yeah, I do,” Dean agreed.

“Well,” Gabe said, leaning back.  “He's not a bum ... he's a rich, classy guy.”

“That's gonna just break my heart ... oh wait,” Dean groaned.

“Hey, Dean ... you don't know what might happen.  You guys could ... I dunno ... buy a couple of horses maybe.  Some diamonds?” Gabe mused.  “It could work.  It happens.”

Dean laughed.  “Yeah?  When does it happen, Gabe?  When does it work out for people like us?”

“Hey, life ain't Disney and you sure as shit ain't Cinder-fuckin'-rella, Dean, but you never know.  Maybe he's your guardian angel ... you said he was named for one.”  Gabe said with a grin.

Dean had to laugh at the thought of Cas with wings.

* * *

Castiel paced the boardroom at Crowley's offices.  He couldn't seem to sit still.  Crowley was all but preening in his seat across from Robert Singer and Joanna Harvelle-Singer. 

“Mr. Singer, you wanted to meet with Mr. Novak ... he is now listening,” Crowley said smugly.

Singer sighed and looked at Castiel.  “I've reconsidered my position on your acquisition offer.  With one condition – I could give a shit about myself, but the people who work for me --”

Crowley waved dismissively.  “Not to worry – they'll be taken care of. Now then, gentlemen, let's address the contracts in front of us.”

Castiel inhaled deeply and said, “Wait, Fergus.  I'd like to speak with Mr. Singer alone.”

Crowley's face darkened.  “What are you talking about, Castiel?”

“I would like to meet with Mr. Singer alone – please.”

“Fine ... gentlemen, please wait outside.”

“Crowley? You too.”  Castiel said softly.

“What the hell are you doing, Castiel?  Why does blondie get to stay?” Crowley said, pointing to Joanna.

Singer bristled but he motioned to Jo and she walked out of the room ahead of Crowley.  Once the door shut, she rounded on the man.  “Call me 'blondie' again, Mr. Crowley, and I'll kick your ass to hell and back.”

Crowley sneered but didn't stand too close to her while they waited.

* * *

In the conference room, Castiel shuttered the blinds against the sun's glare and offered him a cup of coffee.  Singer declined and looked at Castiel.

“What do you want now, Novak?”

Castiel sighed.  “I no longer wish to buy your company and take it apart – it is still vulnerable, however, and I do not want anyone else to attempt a takeover.  I think ... perhaps we can do something special with it.”

Singer listened to Castiel's offer and smiled.  “Why the change of heart, kid?”

Castiel chuckled at the informal address.  “I met someone ... “

* * *

When Crowley re-entered the conference room, Castiel patted him on the shoulder and said, “Wrap it up, Fergus.”

Castiel could hear Crowley's protesting shouts all the way into the hall.  He smiled.

Instead of going back to the hotel, Castiel decided to walk in the park he and Dean had visited the day before.  He slipped off his shoes and walked barefoot for a while.  As he did so, he contemplated his week with Dean and all the ways they'd laughed and enjoyed one another's company.  He thought about Dean's smile – the genuine one that could light a room with its brightness.  He thought about the hazel eyes that changed color in different light. Mostly, Castiel thought about how he was desperately in love with Dean Winchester.

* * *

Dean sighed.  He'd packed up all the clothes and looked around the empty hotel room he'd call home for a few days.  Every room held some memory of his time with Castiel and he was loathe to leave it but he knew his time with the man was at an end.  Walking over to the desk where Castiel had done most of his work at night, Dean smiled.  Jo had called him and told him how he'd saved her step-dad’s company. Dean felt proud of Castiel ... and glad that he'd finally realized that he wasn't quite the heartless mogul he considered himself.

Picking up a pen, Dean decided to leave Castiel a note even though he had no gift for words.  He'd just started when the doorbell rang.  Walking over, he opened it on a face he really didn't want to see.  Crowley.

“Well, if it isn't the streetwalker.  I'm looking for Castiel,” Crowley growled.

Dean ignored the insult.  “Cas ain't here ... I thought he was with you.”

Crowley pushed past Dean and walked toward the bar.  “Oh no, Dean darling – Castiel is definitely not with _me._ I believe that Castiel is with _you_. The Castiel _I_ knew did not blow off billion-dollar deals.  Mind if I have a drink?”

Dean shrugged.  “Help yourself.”

Crowley held out a glass.  “No thanks ... look, Cas is probably gonna be home soon.  I can tell him you came by.”

“Ah ... you see, _there_ is the thing you do not understand, Dean.  _This_ a hotel room ... not 'home'.  _You_ are not the man of the house ... you are just a relatively cheap fuck that Castiel picked up for the week.”  Crowley sat next to Dean on the couch, pressing against him.  “Perhaps you are better at your chosen profession than most ... is that it, Dean?  If I fuck you --” Crowley's hand slid up Dean's thigh and he jerked away.  “If I fuck you, will I join Castiel in his happy-place?  Let's find out ...”

Dean pulled away and stood.  “Back off, asshole – I wouldn’t fuck you if you were the last person on the planet.”

“Really ... are you a discerning hooker now?  Exclusive clientele?” Crowley sneered.

Dean's eyes narrowed.  “Get the fuck out of here, Crowley.  Go screw your wife ... or did you not marry her for _that_ either?”

“You little ---” Crowley said coldly as he moved toward Dean.

Dean had let his guard down around Castiel.  The old Dean would never have allowed Crowley a clear path to him and before he could get out of range, Crowley had him flipped around and slammed over the desk.  Dean's head hit the surface hard and he saw stars for a minute. 

“Get off me!” Dean yelled.

Dean had been attacked by johns before but he until he could get his feet under him, he couldn't buck off Crowley.  The man had an iron grip on his hair and he banged Dean's head down again, stunning him.

“Let's see how you like being fucked with, Dean darling ... maybe I won't care about the millions of dollars Castiel just cost me.  Because at this moment I do care ... I care a great deal.”

Dean felt the man pressing against his ass and he struggled harder to shake off the fuzziness.  “Get off me, fucker!”

Dean's head hit the table again and then the weight on his back was gone. Dean slid to his knees and looked woozily over at Crowley ... and Castiel.

Castiel's face was nothing short of total wrath.  His blue eyes were almost glowing as he dragged Crowley away from Dean.

“What the hell do you think you are doing, Fergus?!?” Castiel snarled.

Crowley looked at Castiel in disbelief.  “He's a _whore_ , Castiel!  A fucking male prostitute and you choose _him_ over me?  He's nothing but a cock-sucking rent -- “

Castiel's fist connected with Crowley's nose, cutting off the rant.  Dean was standing unsteadily behind him, watching the altercation.  “Get out, Crowley!”

Crowley staggered to his feet.  “My nose!  You broke my nose, Castiel!” When Castiel advanced on him threateningly, Crowley looked desperate. “Come on, Castiel!  You've known me for a decade – I dedicated my _life_ to you!”

Castiel tossed Crowley's briefcase out into the hallway.  “You dedicated yourself to your _own_ gain, Crowley.  I've made you a very rich man doing what you love – going in for the kill!  Now – Get. Out.”

Even Dean paused when Castiel's voice dropped into an octave he'd never heard before – one that did not brook disobedience.  Fergus Crowley wisely listened to his own survival instinct and fled.  Castiel slammed the door shut behind him and met Dean's eyes.

* * *

“Man, if I’d a known that desk was so sturdy we coulda had some real fun, Cas,” Dean joked while holding a makeshift icepack to his face. He'd have a bruise but hopefully not a black eye.

Castiel smiled wanly.  “A pity neither of us thought about it, Dean.”

Dean looked over at Castiel.  “Heard what you did with Singer.”

“It was a business decision.”

“It was good, Cas.”

Castiel smiled again.  “It felt good, Dean.”

Dean looked down and then lay the ice pack aside.  “I – uh ... I gotta get goin', Cas.”

“I noticed you packed,” Castiel said softly.  “Why are you leaving now ... today?”

“Cas ... there's always gonna be some jerk who thinks like Crowley.  Who thinks it's allowed like Crowley – even a friend of yours,” Dean said.  “What're you gonna do, Cas?  Be my avenging angel?”

“That isn't why you are leaving, Dean,” Castiel said, studying the cuts on his knuckles.

Dean stood, and for once did not jam his hands into his pockets.  “Look, Cas ... the offer you made me – it's great.  It's tempting.” Dean exhaled slowly.  “A couple of months ago, I woulda been all over it in a heartbeat.  But ... things are different now – you changed that and you can't change it back.  I want more.”

Castiel stood.  He regarded Dean with eyes that threatened his resolve.

“I know about wanting more, Dean.  Who do you suppose invented the concept?”  Castiel smiled in response to Dean's grin.  The smile faded to a soft confusion.  “The question is ... how much more do you want?”

Dean looked at Castiel and answered honestly.  “I want my angel, Cas.”

Turning, Dean grabbed his jacket and slid into it.  He went to put on his shoes and Castiel sat next to him.  “My special gift, Dean – impossible relationships.”  Dean smiled over at him while he tied his laces.

Castiel smiled back and handed over an envelope.  “Thank you, Dean.”

Dean fingered the envelope and then put it in the interior pocket of his jacket.  “You're welcome, Cas.”

Castiel held out a business card.  “Dean, if you ever need anything – perhaps more bubble bath?  Please call me.”

Dean grinned.  He companionably leaned against Castiel's shoulder.  “I had a good time, Cas.”

“I did as well, Dean.”

Picking up the garment bags, Dean walked to the door.  Castiel opened it and then abruptly slammed it shut again.  “Dean ... stay.  Please stay the night with me – not because you feel obligated but because you truly want to.”

Whatever had been holding the tear back relinquished its grip and one drop slid down Dean's cheek.  Castiel brushed it away with his thumb. 

“I can't, Cas,” Dean said hoarsely.  “I wish to God I could.”

Castiel nodded and opened the door again.  “Good-bye, Dean.”

Dean paused in the doorway and looked at Cas.  “You're a pretty special guy, Cas.  Don't let 'em make you forget that again.”

Dean walked to the elevator and Castiel softly shut the door behind him. He leaned his forehead against the door and was surprised to feel something wet on his cheeks. 

* * *

Balthazar had just given directions to one of the bellman when Dean came out into the lobby.  He smiled at the young man.

“Hey, Balthy,” Dean quipped.  “I wanted to say 'bye.”

“I suppose that means you won't be accompanying Mr. Novak to New York?” Balthazar asked with regret.

“Nah. You and me live in the real world, Balthazar – most of the time.” Dean replied.

“Do you have transportation, Dean?”

“I'll just catch a cab.”

“Allow me - “ Balthazar waved over the hotel driver.  “Take Mr. Winchester anywhere he wishes to go.”

Dean grinned and held his hand out to Balthazar who shook it firmly. “It's been ... interesting ... knowing you, Dean.  Drop by to see us again, sometime – you certainly liven things up.”  Balthazar smiled warmly.

“Stay cool, Balthazar.”

* * *

It was raining as the limo headed out.  Dean sat pressed into one corner of the back seat trying desperately not to look back.  He wasn't successful.  He watched until the limo rounded a corner and he could no longer see the hotel.  Dean managed to actually make it to the apartment and put down his bags before losing it entirely.  Gabriel didn't ask, he just sat beside Dean and gently rubbed his back until the shaking stopped.

* * *

Castiel stood on the balcony and watched the lights moving across the city. He wondered if Dean was one of those moving lights.  Clouds were moving in so Castiel could not see the stars.  He sighed and turned in early that night.  He did not sleep much --- he kept waking up and reaching for someone who was no longer there.

The next morning, Castiel packed and had the bags taken downstairs.  He looked out at the incoming rain and listened to distant thunder.  It was fitting weather for his mood.

* * *

Gabriel sadly watched his friend pack.  “You know, San Fran ain't that great – bad climate.  Foggy and unpredictable.”

Dean grinned.  “I'll wear a sweater, _mom_.”

“What're you gonna do there?”

“Get a job ... maybe check out a few vo-tech classes,” Dean said softly. “I'm really good at cars ... I dunno.  Maybe EMT training or somethin'.  I can do whatever I want – just gotta figure out what that is.”

Dean turned and regarded Gabriel for a moment.  “You can still come with, Gabe.”

Gabriel rolled his eyes.  “And leave all this?  Not in a million, Dean-o.”

Dean laughed.  “Fine.  Here.”  Dean handed Gabriel a roll of bills.

“Whoa! What's this?”  Gabriel said in shock.

“Part of the Castiel Novak Scholarship Fund, Gabe.  You got potential, dude.  A lot of it.” Dean said with a grin.

“You think I have potential?” Gabriel asked.  His voice held a note of disbelief that anyone considered him _that_ special.

“Yeah, I do – don't let any of those morons tell you different, ok?” Dean's voice grew hoarse.

“When's your flight?” Gabriel asked softly, fingering the hem of his t-shirt.

“Tonight ... cab'll pick me up.”

“Ok . . . I, uh ... I gotta split, Dean.  Good-byes make me crazy.” Gabriel looked at Dean fondly.  “Take care o' you.”

Dean bumped his fist.  “Take care o' you, man.”

* * *

Castiel signed the bill for his stay and handed it over to Balthazar.  “Do you happen to have any ... messages for me?”

Balthazar regarded Castiel for a moment and shook his head.  “No, I'm sorry, I don't, Mr. Novak.”

“Just as well – I will need a car to the airport.”

“Of course, our driver will take you wherever you need to go,” Balthazar said quietly.  “He also took Mr. Winchester home yesterday.”

Castiel's lips quirked.  “Thank you, Balthazar.”

“Looking forward to your next visit, Mr. Novak.”

* * *

Castiel sat in the limo trying to imagine Dean sitting beside him.  He tried to imagine all the events he attended alone or with someone he truly didn't care about ... and he could only imagine the hazel eyes and the easy grin looking back at him.  Tapping his phone, Castiel canceled his flight and began to make arrangements.

* * *

Dean sat alone in the apartment.   He was doing another circuit around the apartment to ensure he didn't leave anything behind when he heard a loud noise outside – it sounded vaguely like a Led Zeppelin song ... only done with by a string quartet.  Odd.

Opening the window, Dean glanced in the direction of the music that was pounding out of a car stereo.  His eyes registered the car, but he couldn't decide if he was losing his mind or not.  The 1967 black Impala hardtop that was rumbling down the street to park at the curb looked too familiar not to be his Baby.  Then the driver side door opened and someone unfolded to stand beside the car with a grin a mile wide.

“Sammy?!?” Dean yelled.

He was out the window and down the fire escape almost before Sam made it around the car.  The brothers embraced tightly. 

“Sammy ... Sammy is that really you?!?”

“Yeah, Dean ... it's me.” Sam said, his eyes tearing.

Dean shook his head.  “Did you grow like another foot, you freak?”

“Shut up, jerk.”

“You shut up, bitch – how the hell did you know where I was?” Dean asked.

Sam jerked his thumb back to the Impala.  “I got a phone call.”

Castiel got out of the passenger side slowly.  Sam chuckled at the look on his brother's face.

“Cas? You – you did this?”

“I made a few calls, Dean,” Castiel said smiling.

Dean blinked.  “Why, dude?”

“Because I wanted you to believe in angels again, Dean.”

Dean Winchester didn't say anything, he simply closed the distance between them and kissed Castiel.  His mom was right -- there were angels out there and he'd found his own.


End file.
